Cyclohexylamine → HCID 178422224, compound

HRID 1898366Notes

Reaction equation

HRID 1898366 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[CH:19]=[C:20]([CH3:22])[O:21][C:17]=3[C:16]([C:23]([OH:25])=O)=[CH:15][C:13]=2[N:14]=1.F[B-](F)(F)F.[N:31]1(OC(N(C)C)=[N+](C)C)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2N=N1.C1COCC1.C1(N)CCCCC1>CN(C=O)C>[CH:35]1([NH:31][C:23]([C:16]2[C:17]3[O:21][C:20]([CH3:22])=[CH:19][C:18]=3[C:12]3[NH:11][C:10]([NH:9][C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])=[N:14][C:13]=3[CH:15]=2)=[O:25])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:34]1

Participants

6

Reactant 4

HCID 7965CyclohexylamineHCID 8028TetrahydrofuranHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422229HCID 178422229, compound

Product 1

HCID 178422224HCID 178422224, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(2,6-dichlorophenyl)amino]-7-methyl-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-9, 0.050 g, 0.132 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.085 g, 0.265 mmol), TEA (1 mL), THF (5.0 mL), DMF (1.0 mL) and cyclohexyl amine (0.026 g, 0.265 mmol) to afford 0.008 g of the desired product. 1HNMR (DMSO-d6): δ 1.23-1.30 (m, 2H), 1.31-1.36 (m, 4H), 1.89 (m, 4H), 3.85 (m, 1H), 4.19 (s, 3H), 6.74 (s, 1H), 7.41-7.94 (m, 4H), 9.07 (s, 1H), 11.00-12.00 (s, 2H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-7dd1a6463337417bbd4f29121066bde1
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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