methyl 3-{[(1R)-1-(2-chloro-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}phenyl)ethyl]oxy}-5-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-benzimidazol-1-yl]-2-thiophenecarboxylate → Methyl 3-{[(1R)-1-(2-chloro-3-hydroxyphenyl)ethyl]oxy}-5-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-benzimidazol-1-yl]-2-thiophenecarboxylate

HRID 1435139Notes

Reaction equation

HRID 1435139 reaction equation
[Cl:1][C:2]1[C:7]([O:8][Si](C(C)(C)C)(C)C)=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:16]([O:18][C:19]1[CH:23]=[C:22]([N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:33]4[O:34][C:35]([CH3:38])=[N:36][N:37]=4)=[CH:32][C:27]=3[N:26]=[CH:25]2)[S:21][C:20]=1[C:39]([O:41][CH3:42])=[O:40])[CH3:17].ClC1C(O)=CC=CC=1[C@H](OC1C=C(N2C3C=C(C#N)C=CC=3N=C2)SC=1C(OC)=O)C>>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:16]([O:18][C:19]1[CH:23]=[C:22]([N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:33]4[O:34][C:35]([CH3:38])=[N:36][N:37]=4)=[CH:32][C:27]=3[N:26]=[CH:25]2)[S:21][C:20]=1[C:39]([O:41][CH3:42])=[O:40])[CH3:17]

Participants

3

Reactant 2

HCID 59251029methyl 3-{[(1R)-1-(2-chloro-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}phenyl)ethyl]oxy}-5-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-benzimidazol-1-yl]-2-thiophenecarboxylateHCID 68565973methyl 3-[(1R)-1-(2-chloro-3-hydroxyphenyl)ethoxy]-5-(6-cyano-1H-benzimidazol-1-yl)thiophene-2-carboxylate

Product 1

HCID 68565938Methyl 3-{[(1R)-1-(2-chloro-3-hydroxyphenyl)ethyl]oxy}-5-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-benzimidazol-1-yl]-2-thiophenecarboxylateYield 35.1%

Procedure

The title compound was prepared from methyl 3-{[(1R)-1-(2-chloro-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}phenyl)ethyl]oxy}-5-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-benzimidazol-1-yl]-2-thiophenecarboxylate (82.0 mg, 0.312 mmol) using a procedure analogous to Intermediate 3, Step F to give 55.9 mg of the desired product. MS (ESI): 511 [M+H]+.

Sources & evidence

ORD record
ord-5fd5e89b9b1b452c8ce89377d4f41229
Source dataset
uspto-grants-2009_11
Patent number
US07615643B2

Reaction notes

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