4-Methylmorpholine → HCID 178422754, compound

HRID 1898363Notes

Reaction equation

HRID 1898363 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](O)=[O:24])=[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:66])([F:65])[C:58]1[CH:64]=[CH:63][C:61]([NH2:62])=[CH:60][CH:59]=1>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]([CH3:21])([CH3:22])[O:20][C:16]=3[C:15]([C:23]([NH:62][C:61]3[CH:63]=[CH:64][C:58]([C:57]([F:56])([F:65])[F:66])=[CH:59][CH:60]=3)=[O:24])=[CH:14][C:12]=2[N:13]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 99644-(Trifluoromethyl)anilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422814HCID 178422814, compound

Product 1

HCID 178422754HCID 178422754, compoundYield 14.7%

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, 0.100 g, 0.254 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.163 g, 0.509 mmol), N-methyl morpholine (1.0 mL), DMF (1.5 mL), THF (7.0 mL) and 4-trifluoro methyl aniline (0.082 g, 0.509 mmol) to afford 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 1.58 (s, 6H), 3.07 (s, 2H), 7.25 (s, 1H), 7.72 (d, J=8.1 Hz, 2H), 7.90 (d, J=8.4 Hz, 2H), 8.45 (s, 2H), 9.91 (s, 1H), 10.99 (s, 1H), 11.55 (s, 1H); MS [M+H]+: 536.22.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-914a018c5e14404bba72ad55c5e07f6e
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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