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

HRID 1898358Notes

Reaction equation

HRID 1898358 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.[N:32]1(OC(N(C)C)=[N+](C)C)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.CN1CCOCC1.C(N)CCCCC>C1COCC1.CN(C=O)C>[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]([NH:32][CH2:36][CH2:35][CH2:40][CH2:39][CH2:38][CH3:37])=[O:25])=[CH:14][C:12]=2[N:13]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8102HexylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422814HCID 178422814, compound

Product 1

HCID 1784448452-[(3,5-Dichloropyridin-4-yl)amino]-N-hexyl-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxamideYield 16.5%

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, 0.225 mmol), N-methyl morpholine (0.025 g, 0.247 mmol), DMF (0.5 mL), THF (3.0 mL) and n-hexyl amine (0.026 g, 0.257 mmol) to afford 0.010 g of the desired product. 1HNMR (DMSO-d6): δ 0.86 (s, 3H), 1.23 (s, 3H), 1.28 (m, 8H), 1.49 (s, 3H), 3.01 (s, 2H), 7.32-7.33 (m, 2H), 7.21 (s, 1H), 7.69 (s, 1H), 8.43 (s, 2H), 10.91 (s, 1H), 11.39 (s, 1H); MS [M+H]+: 476.33.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-22edd209d8cf416f85813719a98dd789
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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