[Cl:1][C:2]1[C:3]([C:11]([OH:13])=O)=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:14][N:15](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN>CN(C=O)C>[Cl:1][C:2]1[C:3]([C:11]([NH:15][CH3:14])=[O:13])=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]To a solution of 4-chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-3-carboxylic acid (0.075 g, 0.368 mmol) in DMF (1 ml) was added HATU (0.168 g, 0.442 mmol), DIPEA (0.097 ml, 0.553 mmol) and methyl amine (2M in THF) (0.276 ml, 0.553 mmol). The reaction mixture was stirred at RT overnight. Purification was accomplished by HPLC, the desired fractions collected and lypholized to afford methyl 3-chloro-4-[(methylamino)carbonyl]-1H-pyrrole-2-carboxylate (0.046 g, 57.6% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.39 (br. s., 1H) 7.73-7.83 (m, 1H) 7.46 (d, 1H) 3.80 (s, 3H) 2.70 (d, 3H). MS: m/z 217.0 (M+1).
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