Dimethylformamide → HCID 178422774, compound

HRID 1898371Notes

Reaction equation

HRID 1898371 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[CH2:18][C:19]([CH3:22])([CH3:21])[O:20][C:16]=3[C:15]([C:23](O)=[O:24])=[CH:14][C:12]=2[N:13]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN(C=O)C.[Cl:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][CH:55]=1>C1COCC1>[Cl:53][C:54]1[CH:60]=[CH:59][C:57]([NH:58][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:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:13][C:12]=3[CH:14]=2)=[O:24])=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78124-ChloroanilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422812HCID 178422812, compound

Product 1

HCID 178422774HCID 178422774, compoundYield 23.1%

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]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-12, 0.050 g, 0.139 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.089 g, 0.277 mmol), TEA (1.0 mL), DMF (1.0 mL), THF (5.0 mL) and 4-chloro aniline (0.035 g, 0275 mmol) to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.60 (s, 6H), 3.17 (s, 2H), 7.05 (t, J=7.5 Hz, 1H), 7.36-7.43 (m, 2H), 7.49 (d, J=7.8 Hz, 2H), 7.75 (d, J=8.1 Hz, 2H), 8.58-8.60 (m, 1H), 9.07 (s, 1H), 9.87 (s, 1H), 11.02 (s, 1H), 11.36 (s, 1H); MS [M+H]+: 467.23.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-840ef30ec95348cfa40c93cbb96c4748
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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