4-Methylmorpholine → 2-[(3,5-Dichloropyridin-4-yl)amino]-7,7-dimethyl-N-[2-(trifluoromethyl)benzyl]-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxamide

HRID 1898357Notes

Reaction equation

HRID 1898357 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23]([OH:25])=O)=[CH:14][C:12]=2[N:13]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1.[F:56][C:57]([F:67])([F:66])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][C:59]=1[CH2:64][NH2:65]>C1COCC1.CN(C=O)C>[Cl:26][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23]([NH:65][CH2:64][C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][C:58]=3[C:57]([F:56])([F:66])[F:67])=[O:25])=[CH:14][C:12]=2[N:13]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 764472-(Trifluoromethyl)benzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422814HCID 178422814, compound

Product 1

HCID 1784228082-[(3,5-Dichloropyridin-4-yl)amino]-7,7-dimethyl-N-[2-(trifluoromethyl)benzyl]-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxamideYield 21.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-3, 0.050 g, 0.127 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.082 g, 0.255 mmol), N-methyl morpholine (0.5 mL), DMF (1.0 mL), THF (5.0 mL) and 1-[2-(trifluoromethyl)phenyl]methanamine (Intermediate-4, 0.027 g, 0.154 mmol) to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.21 (s, 3H), 1.48 (s, 3H), 3.01 (s, 2H), 4.68 (m, 2H), 7.19 (s, 1H), 7.46-7.51 (m, 2H), 7.62 (d, J=7.8 Hz, 1H), 7.72 (d, J=7.8 Hz, 1H), 8.27 (m, 1H), 8.41 (s, 2H), 10.89 (s, 1H), 11.42 (s, 1H); MS [M+H]+: 550.31.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-8ddb731cffec497b9201588a4038285f
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…