(1R,2R)-2-methoxycarbonylcyclopentane-1-carboxylic acid

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

Procedure: Rac-trans-cyclopentane-1,2-dicarboxylic acid monomethyl ester (86 mg) was dissolved in DMF (5 mL) and treated with HATU (1.1 eq. 214 mg) and DIEA (3 eq, 267 μL) and stirred for 15 minutes. Then 4-(2-amino-thiazol-4-yl)-N-cyclopropyl-benzamide (1 eq, 129.5 mg) was added and the mixture stirred at ambient temperature overnight. The reaction was cooled, filtered and the solvents removed. The resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. Yield 14 mg. MS: 414.5 (M+H+); H1-NMR (DMSO-d6): δ(ppm) 12.4 (s, 1H), 8.4 (m, 2H), 7.9-7.7 (m, 5H), 3.6 (s, 3H), 3.2 (m, 2H), 2.8 (m, 1H), 2.0 (m, 2H), 1.7 (m, 4H) 0.7-0.6 (m, 4H). the mixture stirred at ambient temperature overnight The reaction was cooled filtered the solvents removed The resulting mixture was redissolved in 5 ml of 90% DMF 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product

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

Procedure: Rac-trans-cyclopentane-1,2-dicarboxylic acid monomethyl ester (86 mg) was dissolved in DMF (5 mL) and treated with HATU (1.1 eq. 214 mg) and DIEA (3 eq, 267 μL) and stirred for 15 minutes. Then 4-(2-amino-thiazol-4-yl)-N-cyclopropyl-benzamide (1 eq, 129.5 mg) was added and the mixture stirred at ambient temperature overnight. The reaction was cooled, filtered and the solvents removed. The resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. Yield 14 mg. MS: 414.5 (M+H+); H1-NMR (DMSO-d6): δ(ppm) 12.4 (s, 1H), 8.4 (m, 2H), 7.9-7.7 (m, 5H), 3.6 (s, 3H), 3.2 (m, 2H), 2.8 (m, 1H), 2.0 (m, 2H), 1.7 (m, 4H) 0.7-0.6 (m, 4H). the mixture stirred at ambient temperature overnight The reaction was cooled filtered the solvents removed The resulting mixture was redissolved in 5 ml of 90% DMF 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product

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

Procedure: Rac-trans-cyclopentane-1,2-dicarboxylic acid monomethyl ester (86 mg) was dissolved in DMF (5 mL) and treated with HATU (1.1 eq. 214 mg) and DIEA (3 eq, 267 μL) and stirred for 15 minutes. Then 4-(2-amino-thiazol-4-yl)-N-cyclopropyl-benzamide (1 eq, 129.5 mg) was added and the mixture stirred at ambient temperature overnight. The reaction was cooled, filtered and the solvents removed. The resulting mixture was redissolved in 5 ml of 90% DMF, 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product. Yield 14 mg. MS: 414.5 (M+H+); H1-NMR (DMSO-d6): δ(ppm) 12.4 (s, 1H), 8.4 (m, 2H), 7.9-7.7 (m, 5H), 3.6 (s, 3H), 3.2 (m, 2H), 2.8 (m, 1H), 2.0 (m, 2H), 1.7 (m, 4H) 0.7-0.6 (m, 4H). the mixture stirred at ambient temperature overnight The reaction was cooled filtered the solvents removed The resulting mixture was redissolved in 5 ml of 90% DMF 10% water with 0.1% TFA and purified by reverse phase HPLC to give the product