6-Methylimidazo[2,1-B][1,3]thiazole-5-carboxylic acid → (1S,3S,5S)-3-{[(6-methyl-imidazo[2,1-b]thiazole-5-carbonyl)-amino]-methyl}-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

HRID 2064794Notes

Reaction equation

HRID 2064794 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH2:15])[CH2:12][C@H:11]2[C@@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1[N:18]=[C:19]2[N:23]([C:24]=1[C:25](O)=[O:26])[CH:22]=[CH:21][S:20]2>>[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][NH:15][C:25]([C:24]2[N:23]3[C:19]([S:20][CH:21]=[CH:22]3)=[N:18][C:17]=2[CH3:16])=[O:26])[CH2:12][C@H:11]2[C@@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 3299796-Methylimidazo[2,1-B][1,3]thiazole-5-carboxylic acidHCID 58278675(1S,3S,5S)-tert-Butyl 3-(aminomethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Product 1

HCID 67080943(1S,3S,5S)-3-{[(6-methyl-imidazo[2,1-b]thiazole-5-carbonyl)-amino]-methyl}-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

Procedure

prepared by reaction of (1S,3S,5S)-3-aminomethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester with 6-methyl-imidazo[2,1-b]thiazole-5-carboxylic acid. LC-MS (acidic): tR=0.84 min; [M+H]+=377.1. 1H-NMR (CDCl3): δ=0.54 (bs, 1H); 0.80-0.86 (m, 1H); 1.50 (s, 9H); 1.51-1.58 (m, 1H); 1.77 (bd, J=11.8 Hz, 1H); 2.53-2.61 (m, 1H); 2.68 (s, 3H); 3.17-3.24 (m, 1H); 3.59-3.69 (m, 2H); 4.39-4.45 (m, 1H); 6.84 (d, J=4.3 Hz, 1H); 7.79 (bs, 1H); 8.27 (d, J=4.4, 1H).

Sources & evidence

ORD record
ord-4b49e9ef48684e0aa387d95300747ba7
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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