Cyclohexylamine → HCID 178422225, compound

HRID 1898365Notes

Reaction equation

HRID 1898365 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH:18]=[C:19]([CH3:21])[O:20][C:16]=3[C:15]([C:22](O)=[O:23])=[CH:14][C:12]=2[N:13]=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:22]([C:15]2[C:16]3[O:20][C:19]([CH3:21])=[CH:18][C:17]=3[C:11]3[NH:10][C:9]([NH:8][C:7]4[C:6]([Cl:25])=[CH:5][N:4]=[CH:3][C:2]=4[Cl:1])=[N:13][C:12]=3[CH:14]=2)=[O:23])[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 178422230HCID 178422230, compound

Product 1

HCID 178422225HCID 178422225, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(3,5-dichloropyridin-4-yl)amino]-7-methyl-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-8, 0.050 g, 0.132 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.085 g, 0.265 mmol), THF (5.0 mL), DMF (1.0 mL) and cyclohexyl amine (0.026 g, 0.265 mmol) to afford 0.020 g of the desired product. 1HNMR (DMSO-d6): δ 1.23 (s, 3H), 1.36 (t, J=9.6 Hz, 3H), 1.71 (m, 2H), 1.88 (m, 2H), 2.50 (s, 3H), 3.84 (m, 1H), 6.62 (s, 1H), 7.31 (m, 1H), 7.75 (d, J=7.8 Hz, 1H), 8.44 (s, 2H), 11.23 (s, 1H), 11.74 (s, 1H); MS [M+H]+: 458.38.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-144815097a804982a1c24feb230b2054
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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