Chlorosuccinimide → N-[(1S)-2-amino-1-phenylethyl]-4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxamide

HRID 1845632Notes

Reaction equation

HRID 1845632 reaction equation
CN1C([C:7]2C=C(C(O)=O)[S:10][CH:11]=2)=CC=N1.[Br:15]N1C(=O)CCC1=O.Cl[N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=O.[NH2:31][CH:32]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)CNC(=O)OC(C)(C)C.[NH2:49][CH:50](CC1C=CC=CC=1)[CH2:51][CH2:52][NH:53][C:54](=O)OC(C)(C)C>>[NH2:31][CH2:32][C@@H:42]([NH:24][C:28]([C:27]1[S:10][C:11]([CH3:7])=[C:25]([C:52]2[N:53]([CH3:54])[N:49]=[CH:50][C:51]=2[Br:15])[CH:26]=1)=[O:29])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 5

HCID 31398ChlorosuccinimideHCID 67184N-bromobutanimideHCID 20159911tert-butyl N-(2-amino-3-phenylpropyl)carbamateHCID 578264554-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic AcidHCID 597772381,1-Dimethylethyl (3-amino-4-phenylbutyl)carbamate

Product 1

HCID 57826839N-[(1S)-2-amino-1-phenylethyl]-4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-methyl-2-thiophenecarboxamide

Procedure

The title compound was prepared as a white solid according to the procedure of Example 24, except substituting 5-methyl-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid (168 mg, 0.5 mmol) [prepared according to Example 198] for 4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid, N-bromosuccinimide (88.5 mg, 0.5 mmol) for N-chlorosuccinimide and 1,1-dimethylethyl (2-amino-3-phenylpropyl)carbamate (71 mg, 0.3 mmol) [prepared according to the procedure of Preparation 1] for 1,1-dimethylethyl (3-amino-4-phenylbutyl)carbamate: LC-MS (ES) m/z 341 (M+H)+, 1H NMR (400 MHz, MeOD) δ ppm 2.39 (d, J=4.04 Hz, 3H) 3.42 (br. s., 1H) 3.55 (br. s., 1H) 3.75-3.78 (m, 3H) 5.45 (m, 1H) 7.37 (d, J=7.07 Hz, 1H) 7.40-7.46 (m, 2H) 7.49 (br. s., 2H) 7.59-7.68 (m, 1H) 7.80-7.88 (m, 1H).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-077f4a899fbd4114ae54bd826668a576
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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