2-Bromo-imidazo[2,1-b]thiazol-6-ylamine hydrochloride → (S,S)-{1-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

HRID 716512Notes

Reaction equation

HRID 716512 reaction equation
Cl.BrC1SC2=NC(N)=CN2C=1.[C:12]([O:16][C:17](=[O:45])[NH:18][C@@H:19]([C:39]1[CH:44]=CC=C[CH:40]=1)[C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[C:27](=[O:38])[NH:28][C:29]1[N:30]=[C:31]2[N:35]([CH:36]=1)[CH:34]=[C:33]([Br:37])[S:32]2)=[O:21])(C)(C)C>>[CH3:12][O:16][C:17](=[O:45])[NH:18][C@H:19]([C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[C:27](=[O:38])[NH:28][C:29]1[N:30]=[C:31]2[N:35]([CH:36]=1)[CH:34]=[C:33]([Br:37])[S:32]2)=[O:21])[CH:39]([CH3:44])[CH3:40]

Participants

3

Reactant 2

HCID 672405282-Bromo-imidazo[2,1-b]thiazol-6-ylamine hydrochlorideHCID 86654641(S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 67241387(S,S)-{1-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidine-1-carbonyl]-2-methyl-propyl}-carbamic acid methyl ester

Procedure

Compound 12b was synthesized from compound 11 (0.33 mmol) and compound 3b (0.495 mmol), following the procedure as described for compound 12a, to give compound 12b as a yellow oil in 44% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 0.93 (dd, 6H), 1.70-2.00 (m, 4H), 2.01-2.10 (m, 1H), 3.51 (s, 3H), 3.59 (m, 1H), 3.82 (m, 1H), 4.00 (t, 1H), 4.51 (dd, 1H), 7.34 (d, 1H), 7.80 (s, 1H), 8.15 (s, 1H), 10.64 (s, 1H); MS (ESI, EI+) m/z=472-474 (MH+).

Sources & evidence

ORD record
ord-d231294f2c634ba0aa6285afcaebf22f
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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