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,R)-[1-(2-{5-[4-(6-{[1-(2-ethoxycarbonylamino-2-phenylacetyl)-pyrrolidine-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 716534Notes

Reaction equation

HRID 716534 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[NH:5][C@@H:6]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@@H:10]1[C:14](=[O:25])[NH:15][C:16]1[N:17]=[C:18]2[N:22]([CH:23]=1)[CH:21]=[C:20](Br)[S:19]2)=[O:8])[CH3:2].[CH3:33][O:34][C:35](=[O:68])[NH:36][C@H:37]([C:41]([N:43]1[CH2:47][CH2:46][CH2:45][C@H:44]1[C:48]1[NH:49][C:50]([C:53]2[CH:58]=[CH:57][C:56](B3OC(C)(C)C(C)(C)O3)=[CH:55][CH:54]=2)=[CH:51][N:52]=1)=[O:42])[CH:38]([CH3:40])[CH3:39]>>[CH3:33][O:34][C:35](=[O:68])[NH:36][C@H:37]([C:41]([N:43]1[CH2:47][CH2:46][CH2:45][C@H:44]1[C:48]1[NH:49][C:50]([C:53]2[CH:54]=[CH:55][C:56]([C:20]3[S:19][C:18]4=[N:17][C:16]([NH:15][C:14]([C@@H:10]5[CH2:11][CH2:12][CH2:13][N:9]5[C:7](=[O:8])[C@H:6]([NH:5][C:4]([O:3][CH2:1][CH3:2])=[O:32])[C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)=[O:25])=[CH:23][N:22]4[CH:21]=3)=[CH:57][CH:58]=2)=[CH:51][N:52]=1)=[O:42])[CH:38]([CH3:40])[CH3:39]

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 67240827(S,R)-{2-[2-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-pyrrolidin-1-yl]-2-oxo-1-phenylethyl}-carbamic acid ethyl ester

Product 1

HCID 67242208(S,S,S,R)-[1-(2-{5-[4-(6-{[1-(2-ethoxycarbonylamino-2-phenylacetyl)-pyrrolidine-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 11%

Procedure

Compound A55 was synthesized from compounds 44 (0.125 mmol) and 8 (0.187 mmol), following the procedure as described for compound A1, to give compound A55 as a lyophilized white solid in 11% yield. MS (ESI, EI+) m/z=810.2 (MH+).

Workup

  1. customto give compound A55 as a lyophilized white solid in 11% yield

Sources & evidence

ORD record
ord-e17645a2495a4836b9fa8a9f40e09bb4
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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