p-Aminophenylacetic acid ethyl ester → (4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-phenyl)-acetic acid ethyl ester

HRID 1161332Notes

Reaction equation

HRID 1161332 reaction equation
C(OC(=O)C1C=CC(N[C:12](=[O:38])[CH:13]([N:20]2[C:24]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:23]=3[N:22]=[C:21]2[C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=CC=1)C.ClC1C=CC(C2N(C(C3CCCCC3)C(NC[C@H]3CC[C@H](C(O)=O)CC3)=O)C3C=CC(F)=CC=3N=2)=CC=1.[CH2:77]([O:79][C:80](=[O:89])[CH2:81][C:82]1[CH:87]=[CH:86][C:85]([NH2:88])=[CH:84][CH:83]=1)[CH3:78].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>>[CH2:77]([O:79][C:80](=[O:89])[CH2:81][C:82]1[CH:83]=[CH:84][C:85]([NH:88][C:12](=[O:38])[CH:13]([N:20]2[C:24]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:23]=3[N:22]=[C:21]2[C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)=[CH:86][CH:87]=1)[CH3:78]

Participants

5

Reactant 4

HCID 225219p-Aminophenylacetic acid ethyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 686454934-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-benzoic acid ethyl esterHCID 178523387HCID 178523387, compound2×

Product 1

HCID 68645476(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-phenyl)-acetic acid ethyl esterYield 82%

Procedure

This compound was synthesized in analogy to example 22, intermediate d, from [2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetic acid (example 20, intermediate c), (4-amino-phenyl)-acetic acid ethyl ester and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate to give the desired compound as a yellow foam (82%).

Sources & evidence

ORD record
ord-33fbffec567449ecbac042f50071a0d4
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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