Diisopropylethylamine → [Rac]-3-(4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2h-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenyl)-propionic acid tert-butyl ester

HRID 1678690Notes

Reaction equation

HRID 1678690 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([CH:17]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:18](O)=[O:19])=[C:15]3[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)=[N:9]2)=[CH:4][CH:3]=1.[C:27]([O:31][C:32](=[O:43])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[C:37]([F:42])[CH:36]=1)([CH3:30])([CH3:29])[CH3:28].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:27]([O:31][C:32](=[O:43])[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([NH:41][C:18](=[O:19])[CH:17]([C:16]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=[C:10]3[C:15]=2[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)=[C:37]([F:42])[CH:36]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66905628Tert-butyl 3-(4-amino-3-fluorophenyl)propanoateHCID 67131112[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid

Product 1

HCID 67131031[Rac]-3-(4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2h-indazol-3-yl]-2-cyclohexyl-acetylamino}-3-fluoro-phenyl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described in example 59, [2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-cyclohexyl-acetic acid (example 5.1) was reacted with 3-(4-amino-3-fluoro-phenyl)-propionic acid tert-butyl ester in the presence of DIPEA and HATU in DMF to give the title compound yellow solid.

Sources & evidence

ORD record
ord-fd358195e16e4c0fba96e797fc5ef911
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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