2-(4-Amino-3-fluorophenyl)propanoic acid → 2-(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenyl)-propionic acid ethyl ester

HRID 1161333Notes

Reaction equation

HRID 1161333 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.Cl[C:41]1C=CC(C2N(C(C3CCCCC3)C(NC[C@H]3CC[C@H](C(O)=O)CC3)=O)C3C=CC(F)=CC=3N=2)=C[CH:42]=1.[NH2:77][C:78]1[CH:83]=[CH:82][C:81]([CH:84]([CH3:88])[C:85]([OH:87])=[O:86])=[CH:80][C:79]=1[F:89]>CN(C)C1C=CN=CC=1>[CH2:41]([O:86][C:85](=[O:87])[CH:84]([C:81]1[CH:82]=[CH:83][C:78]([NH:77][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[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:79]([F:89])[CH:80]=1)[CH3:88])[CH3:42]

Participants

5

Reactant 3

HCID 130652312-(4-Amino-3-fluorophenyl)propanoic acidHCID 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 686457182-(4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The title 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), 2-(4-amino-3-fluoro-phenyl)-propionic acid and using 4-(dimethylamino)pyridine as a base.

Sources & evidence

ORD record
ord-a935ade86367411a92ebb88bd09f2f7a
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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