4,5-Dibromothenoic acid → N-[(1S)-2-amino-1-phenylethyl]-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

HRID 2392226Notes

Reaction equation

HRID 2392226 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([OH:10])=O)[S:5][C:6]=1Br.CC([N:15]([CH2:19][C@@H:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)C(=O)[O-])(C)C.[NH2:28][CH:29](CC1C=CC=CC=1)[CH2:30][CH2:31][NH:32][C:33](=O)OC(C)(C)C>>[NH2:15][CH2:19][C@@H:20]([NH:27][C:8]([C:4]1[S:5][CH:6]=[C:2]([C:31]2[N:32]([CH3:33])[N:28]=[CH:29][CH:30]=2)[CH:3]=1)=[O:10])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 806114,5-Dibromothenoic acidHCID 597772381,1-Dimethylethyl (3-amino-4-phenylbutyl)carbamateHCID 866335631,1-dimethylethyl[(2S)-2-amino-2-phenylethyl]carbamate

Product 1

HCID 57826695N-[(1S)-2-amino-1-phenylethyl]-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

Procedure

The title compound was prepared as a white solid according to the procedure of Example 20, except substituting 4-bromo-2-thiophenecarboxylic acid (83 mg, 0.4 mmol) for 4,5-dibromo-2-thiophenecarboxylic acid and substituting 1,1-dimethylethyl[(2S)-2-amino-2-phenylethyl]carbamate (94 mg, 0.4 mmol) [prepared according to the procedure of Preparation 1] for 1,1-dimethylethyl (3-amino-4-phenylbutyl)carbamate: LC-MS (ES) m/z 327 (M+H)+, 1H NMR (400 MHz, MeOD) δ ppm 3.44 (d, J=2.78 Hz, 1H) 3.60 (br. s., 1H) 4.06 (br. s., 3H) 5.47 (dd, J=10.36, 4.29 Hz, 1H) 6.70 (br. s., 1H) 7.38 (d, J=6.82 Hz, 1H) 7.44 (t, J=7.20 Hz, 2H) 7.53 (d, J=7.58 Hz, 2H) 7.79 (br. s., 1H) 8.04 (br. s., 1H) 8.32 (br. s., 1H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-b0016956a54045c2bee48c8e0f9623a0
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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