Dimethylformamide → tert-Butyl 4-(5-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate

HRID 592488Notes

Reaction equation

HRID 592488 reaction equation
CN(C=O)C.[C:6]([C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]#[C:19][C:20]2[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][N:23]=[C:22]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([CH:37]4[CH2:42][CH2:41][N:40]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:39][CH2:38]4)=[N:35][CH:36]=3)[N:21]=2)[CH2:11][CH2:10]1)(=[O:8])[NH2:7]>[Pd].CCN(CC)CC>[C:6]([C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][CH2:19][C:20]2[C:25]([C:26]([F:29])([F:28])[F:27])=[CH:24][N:23]=[C:22]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([CH:37]4[CH2:38][CH2:39][N:40]([C:43]([O:45][C:46]([CH3:47])([CH3:48])[CH3:49])=[O:44])[CH2:41][CH2:42]4)=[N:35][CH:36]=3)[N:21]=2)[CH2:11][CH2:10]1)(=[O:8])[NH2:7]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86712348tert-Butyl 4-(5-((4-((2-(1-carbamoylcyclopropyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate

Product 1

HCID 86712293tert-Butyl 4-(5-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

DMF (3 mL) and Et3N (0.30 mL) were added to a mixture of tert-butyl 4-(5-((4-((2-(1-carbamoylcyclopropyl)phenyl)ethynyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate A78 (0.118 g, 0.194 mmol) and 10% Pd/C (0.182 g). The mixture was stirred under a hydrogen atmosphere for 20 hours, filtered through Celite and the filtrate concentrated under reduced pressure. Purification by silica gel column chromatography (0-100% EtOAc in Petroleum Benzine 40-60° C.) gave the title compound A79 (0.080 g, 67%). LCMS-A: rt 5.852 min; m/z 611.3 [M+H]+.

Workup

  1. filtrationfiltered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customPurification by silica gel column chromatography (0-100% EtOAc in Petroleum Benzine 40-60° C.)

Sources & evidence

ORD record
ord-4b1df4d1ad554a82bb3dc8333b2563ed
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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