Methyl ((S)-3-methyl-1-oxo-1-((S)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-yl)carbamate → (S,S) [2-(4-{2-[1-(2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-imidazo[2,1-b]thiazol-6-yl]-carbamic acid tert-butyl ester

HRID 716518Notes

Reaction equation

HRID 716518 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[N:9]=[C:10]2[N:14]([CH:15]=1)[CH:13]=[C:12](Br)[S:11]2)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20](=[O:53])[NH:21][C@H:22]([C:26]([N:28]1[CH2:32][CH2:31][CH2:30][C@H:29]1[C:33]1[NH:34][C:35]([C:38]2[CH:43]=[CH:42][C:41](B3OC(C)(C)C(C)(C)O3)=[CH:40][CH:39]=2)=[CH:36][N:37]=1)=[O:27])[CH:23]([CH3:25])[CH3:24]>>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[N:9]=[C:10]2[N:14]([CH:15]=1)[CH:13]=[C:12]([C:41]1[CH:42]=[CH:43][C:38]([C:35]3[NH:34][C:33]([C@@H:29]4[CH2:30][CH2:31][CH2:32][N:28]4[C:26](=[O:27])[C@@H:22]([NH:21][C:20]([O:19][CH3:18])=[O:53])[CH:23]([CH3:25])[CH3:24])=[N:37][CH:36]=3)=[CH:39][CH:40]=1)[S:11]2)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 57462153Methyl ((S)-3-methyl-1-oxo-1-((S)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidin-1-yl)butan-2-yl)carbamateHCID 58310246(2-Bromo-imidazo[2,1-b]thiazol-6-yl)-carbamic acid tert-butyl ester

Product 1

HCID 68329041(S,S) [2-(4-{2-[1-(2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-imidazo[2,1-b]thiazol-6-yl]-carbamic acid tert-butyl esterYield 22%

Procedure

Compound A35 was synthesized from compound 10 (0.126 mmol) and compound 8 (0.164 mmol), following the procedure as described for compound A1, as a white lyophilized solid in 22% yield. MS (ESI, EI+) m/z=608.35 (MH+).

Sources & evidence

ORD record
ord-3f863ef0178c42818c16c6fd0ba35fbe
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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