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

HRID 1898356Notes

Reaction equation

HRID 1898356 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.C1(N)CCCCC1>C1COCC1.CN(C=O)C>[CH:36]1([NH:32][C:23]([C:15]2[C:16]3[O:20][C:19]([CH3:22])([CH3:21])[CH2:18][C:17]=3[C:11]3[NH:10][C:9]([NH:8][C:7]4[C:2]([Cl:1])=[CH:3][N:4]=[CH:5][C:6]=4[Cl:26])=[N:13][C:12]=3[CH:14]=2)=[O:25])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:35]1

Participants

7

Reactant 4

HCID 7965CyclohexylamineHCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422814HCID 178422814, compound

Product 1

HCID 178422745N-Cyclohexyl-2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxamideYield 8.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution 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) in mixture of DMF (0.5 mL) and THF (3.0 mL), were added O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.082 g, 0.255 mmol, TBTU), N-methyl morpholine (1.0 mL). The reaction mass was stirred at RT for 30 minutes. Then to the reaction mass added cyclohexyl amine (0.020 g, 0.202 mmol). The reaction mass was stirred at RT for 14-16 h. The reaction mass was quenched in water and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate and dilute HCl solution, and dried over anhydrous sodium sulphate and concentrated to afford 0.005 g of the desired product. 1HNMR (DMSO-d6): δ 1.15-1.35 (m, 7H), 1.48 (s, 3H), 1.58 (m, 2H), 1.79 (m, 2H), 3.00-3.07 (m, 4H), 3.80 (m, 1H), 7.20 (s, 1H), 7.66 (d, J=7.5 Hz, 1H), 8.41 (s, 2H), 10.89 (s, 1H), 11.39 (s, 1H); MS [M−H]−: 472.43.

Workup

  1. stirringThe reaction mass was stirred at RT for 14-16 h
  2. customThe reaction mass was quenched in water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with sodium bicarbonate and dilute HCl solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-103db1f804654a09a640248a7f9efc54
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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