Dimethylformamide → HCID 178422223, compound

HRID 1898369Notes

Reaction equation

HRID 1898369 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=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:30]1(OC(N(C)C)=[N+](C)C)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2N=N1.CN(C=O)C.C1(N)CCCCC1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=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]([NH:30][CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:33]3)=[O:23])=[CH:14][C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7965CyclohexylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422228HCID 178422228, compound

Product 1

HCID 178422223HCID 178422223, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(2-chlorophenyl)amino]-7-methyl-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-11, 0.050 g, 0.146 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.094 g, 0.293 mmol), TEA (1.0 mL), DMF (1.0 mL), THF (5.0 mL) and cyclohexyl amine (0.029 g, 0293 mmol) to afford 0.016 g of the desired product. 1HNMR (DMSO-d6): δ 1.23-1.39 (m, 4H), 1.39-1.52 (m, 1H), 1.58 (m, 1H), 1.74 (m, 2H), 1.90 (m, 2H), 3.33 (m, 3H), 3.88 (m, 1H), 6.85 (s, 1H), 7.05 (m, 1H), 7.40 (t, J=7.2 Hz, 1H), 7.50 (d, J=7.8 Hz, 1H), 7.61-7.70 (m, 2H), 8.62 (s, 1H), 10.20 (s, 1H), 11.25 (s, 1H); MS [M+H]+: 423.41.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f347d096637e4eb1b493a39a8eaf805b
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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