2-chloro-N,N-dimethylacetamide → 6-(4-(2-(1-(2-dimethylamino-2-oxoethyl)piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517941Notes

Reaction equation

OC(C(F)(F)F)=O.[CH3:8][N:9]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)=[C:20]([C:33]([F:36])([F:35])[F:34])[CH:19]=3)[N:14]=[C:13]([C:37]#[N:38])[C:12]=2[N:11]=[N:10]1.Cl[CH2:40][C:41]([N:43]([CH3:45])[CH3:44])=[O:42].CCN(C(C)C)C(C)C>CO>[CH3:44][N:43]([CH3:45])[C:41](=[O:42])[CH2:40][N:30]1[CH2:29][CH2:28][CH:27]([CH2:26][CH2:25][O:24][C:21]2[CH:22]=[CH:23][C:18]([C:15]3[N:14]=[C:13]([C:37]#[N:38])[C:12]4[N:11]=[N:10][N:9]([CH3:8])[C:17]=4[CH:16]=3)=[CH:19][C:20]=2[C:33]([F:36])([F:35])[F:34])[CH2:32][CH2:31]1

Participants

Conditions

Temperature: 90 °C

Procedure

To 1-methyl-6-(4-(2-(piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile TFA salt (150 mg) in methanol (2 ml) was added 2-chloro-N,N-dimethylacetamide (67 mg) and DIPEA (0.23 ml). The mixture was heated at 90° C. for 40 minutes, then purified by basic HPLC to give 6-(4-(2-(1-(2-dimethylamino-2-oxoethyl)piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile which was then converted to HCl salt by lypholising with 1M hydrochloric acid (1 ml) (130 mg).

Workup

custompurified by basic HPLC

Sources & evidence

ORD record: ord-c11a49ecf7ff4eb3b4a7f29345c423d0
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115126B2

Reaction notes

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