1-Chloro-N,N-2-trimethylpropenylamine → N-(3-tert.-Butyl-isoxazol-5-yl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 1189690Notes

Reaction equation

HRID 1189690 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=[C:4]([Cl:16])[C:3]=1[NH:17][C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[C:25]([N:31]3[CH2:36][CH2:35][CH:34]([C:37]([F:40])([F:39])[F:38])[CH2:33][CH2:32]3)[C:26]([C:28](O)=[O:29])=[CH:27][C:20]=2[N:19]=1.[NH2:41][C:42]1[O:46][N:45]=[C:44]([C:47]([CH3:50])([CH3:49])[CH3:48])[CH:43]=1.ClC(N(C)C)=C(C)C>C1COCC1>[C:47]([C:44]1[CH:43]=[C:42]([NH:41][C:28]([C:26]2[C:25]([N:31]3[CH2:36][CH2:35][CH:34]([C:37]([F:39])([F:38])[F:40])[CH2:33][CH2:32]3)=[CH:24][C:21]3[N:22]([CH3:23])[C:18]([NH:17][C:3]4[C:4]([Cl:16])=[CH:5][CH:6]=[C:7]([CH2:8][NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:12])[CH3:13])[C:2]=4[Cl:1])=[N:19][C:20]=3[CH:27]=2)=[O:29])[O:46][N:45]=1)([CH3:50])([CH3:49])[CH3:48]

Participants

5

Reactant 3

HCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 20956943-Tert-butyl-1,2-oxazol-5-amineHCID 679575572-{2,6-Dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 67957442N-(3-tert.-Butyl-isoxazol-5-yl)-2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is prepared in analogy to 1b from 2-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenylamino}-6-[4-trifluoromethyl-piperidinyl]-1-methyl-1H-benzimidazole-5-carboxylic acid (100 mg, 0.16 mmol), 5-amino-3-tert.-butyl-isoxazole (23 mg, 0.16 mmol), (1-chloro-2-methyl-propenyl)-dimethylamine (0.026 mL, 0.20 mmol) TEA (0.114 mL, 0.81 mmol) and THF.

Sources & evidence

ORD record
ord-7d8e4acb47fe4d89adec24b21a05b32b
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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