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,S,S)-[1-(2-{5-[4-(6-{[1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-carbonyl]-amino}-imidazo[2,1-b]thiazol-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

HRID 716523Notes

Reaction equation

HRID 716523 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].[CH3:35][O:36][C:37](=[O:70])[NH:38][C@H:39]([C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[C:50]1[NH:51][C:52]([C:55]2[CH:60]=[CH:59][C:58](B3OC(C)(C)C(C)(C)O3)=[CH:57][CH:56]=2)=[CH:53][N:54]=1)=[O:44])[CH:40]([CH3:42])[CH3:41]>>[CH3:35][O:36][C:37](=[O:70])[NH:38][C@H:39]([C:43]([N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[C:50]1[NH:51][C:52]([C:55]2[CH:56]=[CH:57][C:58]([C:22]3[S:21][C:20]4=[N:19][C:18]([NH:17][C:16]([C@@H:12]5[CH2:13][CH2:14][CH2:15][N:11]5[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]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[O:27])=[CH:25][N:24]4[CH:23]=3)=[CH:59][CH:60]=2)=[CH:53][N:54]=1)=[O:44])[CH:40]([CH3:42])[CH3:41]

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 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 68329046(S,S,S,S)-[1-(2-{5-[4-(6-{[1-(2-tert-butoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-carbonyl]-amino}-imidazo[2,1-b]thiazol-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl esterYield 10%

Procedure

Compound A38 was synthesized from compound 23 (0.091 mmol) and compound 8 (0.137 mmol), following the procedure as described for compound A1 (reaction time=1 hr), as a white lyophilized powder in 10% yield. MS (ESI, EI+) m/z=838.39 (MH+)

Sources & evidence

ORD record
ord-70bf4d653d4d42faa1b83eb46a1d56d2
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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