tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate → (S,S)-[4-(6-{[1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidine-2-carbonyl]-amino}-imidazo[2,1-b]thiazol-2-yl)-phenyl]-carbamic acid tert-butyl ester

HRID 716522Notes

Reaction equation

HRID 716522 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:27])[NH:17][C:18]1[N:19]=[C:20]2[N:24]([CH:25]=1)[CH:23]=[C:22](Br)[S:21]2)=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:35]([NH:42][C:43]1[CH:48]=[CH:47][C:46](B2OC(C)(C)C(C)(C)O2)=[CH:45][CH:44]=1)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>>[C:38]([O:37][C:35](=[O:36])[NH:42][C:43]1[CH:44]=[CH:45][C:46]([C:22]2[S:21][C:20]3=[N:19][C:18]([NH:17][C:16]([C@@H:12]4[CH2:13][CH2:14][CH2:15][N:11]4[C:9](=[O:10])[C@@H:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:34])[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:27])=[CH:25][N:24]3[CH:23]=2)=[CH:47][CH:48]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

3

Reactant 2

HCID 2734617tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamateHCID 67241361(S,S) {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 68328605(S,S)-[4-(6-{[1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidine-2-carbonyl]-amino}-imidazo[2,1-b]thiazol-2-yl)-phenyl]-carbamic acid tert-butyl esterYield 5%

Procedure

Compound A37 was synthesized from compound 23 (0.100 mmol) and 4-(Boc-amino)benzeneboronic acid pinacol ester (0.150 mmol), following the procedure as described for compound A1, as a white lyophilized powder in 5% yield. MS (ESI, EI+) m/z=661.27 (MH+)

Sources & evidence

ORD record
ord-50efe9a94d9f48c8bbbf936a7c41fd42
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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