1-(3-methoxypropyl)piperazine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is synthesized by coupling of 1-(3-Methoxy-propyl)-piperazine (commercially available from CHESS GmbH) and bromoacetonitrile analogously to the preparation of Intermediate 149.2 as a colorless oil; ES-MS: M+=198.2: 1HNMR(DMSO-d6) 3.65 (s, 2H), 3.30 (s, 3H), 2.45-2.20 (m, 12H), 1.65-1.55 (m, 2H). analogously to the preparation of Intermediate 149.2 as a colorless oil

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a similar manner to Step 1 of Example 224, bromide was obtained from (E)-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}methanol (0.30 g, 1.0 mmol) obtained in Step 1 of Example 306, carbon tetrabromide (1.0 g, 3.1 mmol) and triphenylphosphine (0.80 mg, 3.1 mmol). Further, in a similar manner to Step 2 of Example 224, a crude product was obtained from DMF (6.0 mL) and 1-(3-methoxypropyl)piperazine (0.48 g, 3.1 mmol), triethylamine (0.43 mL, 3.1 mmol) and THF (6.0 mL), and the product was used for next step without isolation. In a similar manner to Example 2, the crude product was treated with tin (0.39 g, 3.3 mmol), concentrated hydrochloric acid (1.4 mL) and ethanol (8.9 mL), to obtain (E)-2-[2-(1H-indazol-3-yl)vinyl]-5-[4-(3-methoxypropyl)piperazin-1-ylmethyl]phenylamine (0.34 g, 81%).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 1-(4-chlorophenyl)-3-mesyloxymethyl-2-pyrrolidinone and 1-(3-methoxypropyl)piperazine, in the same manner as in Preparation Example 1(8).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from 1-piperazinepropanol in the same manner as in Preparation Example 9(1) to (4).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(4-tert-butyl-2-isopropoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 1-(3-methoxy-propyl)-piperazine (Aldrich) to give the title compound. HR-MS (ES, m/z) calculated for C39H51N4O3Cl2 [(M+H)+] 693.3333, observed 693.3334.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(4-tert-butyl-2-isopropoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride was reacted with 1-(3-methoxy-propyl)-piperazine (Aldrich) to give the title compound. HR-MS (ES, m/z) calculated for C39H51N4O3Cl2 [(M+H)+] 693.3333, observed 693.3334.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a manner analogous to the method described in examples 8, (4S,5R)-2-(6-tert-butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 51) was coupled with 1-(3-methoxy-propyl)-piperazine (Oakwood) to give the title compound. HR-MS (ES, m/z) calculated for C37H48Cl2N5O3 [(M+H)+] 680.3129, observed 680.3133.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound is synthesized by coupling of 1-(3-Methoxy-propyl)-piperazine (commercially available from CHESS GmbH) and bromoacetonitrile analogously to the preparation of Intermediate 149.2 as a colorless oil; ES-MS: M+=198.2: 1HNMR(DMSO-d6) 3.65 (s, 2H), 3.30 (s, 3H), 2.45-2.20 (m, 12H), 1.65-1.55 (m, 2H). analogously to the preparation of Intermediate 149.2 as a colorless oil