4-Methylmorpholine → HCID 178446461, compound

HRID 1898362Notes

Reaction equation

HRID 1898362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24](O)=[O:25])=[CH:15][C:13]=2[N:14]=1.F[B-](F)(F)F.[N:32]1(OC(N(C)C)=[N+](C)C)[C:36]2C=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.CN1CCOCC1.C(N)CCCC>C1COCC1.CN(C=O)C>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:18]3[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([NH:32][CH2:36][CH2:35][CH2:40][CH2:39][CH3:38])=[O:25])=[CH:15][C:13]=2[N:14]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8060PentylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422813HCID 178422813, compound

Product 1

HCID 178446461HCID 178446461, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(2,6-dichlorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-6, 0.070 g, 0.178 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.114 g, 0.306 mmol), N-methyl morpholine (1.0 mL), DMF (1.0 mL), THF (5.0 mL) and pentan-1-amine (0.031 g, 0.356 mmol) to afford 0.025 g of the desired product. 1HNMR (DMSO-d6): δ 0.880 (m, 3H), 1.23-1.33 (m, 8H), 1.49 (s, 6H), 3.03 (s, 2H), 7.19 (m, 1H), 7.32 (s, 1H), 7.50 (d, J=7.8 Hz, 2H), 7.71 (s, 1H), 10.50-11 (s, 2H); MS [M+H]+: 461.55.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-76c5499a67dc4abfa27851cb4e6693f1
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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