Dimethylformamide → HCID 178422740, compound

HRID 1898364Notes

Reaction equation

HRID 1898364 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[CH2:19][C:20]([CH3:23])([CH3:22])[O:21][C:17]=3[C:16]([C:24]([OH:26])=O)=[CH:15][C:13]=2[N:14]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN(C=O)C.[Br:54][C:55]1[CH:61]=[CH:60][C:58]([NH2:59])=[CH:57][CH:56]=1>C1COCC1>[Br:54][C:55]1[CH:61]=[CH:60][C:58]([NH:59][C:24]([C:16]2[C:17]3[O:21][C:20]([CH3:22])([CH3:23])[CH2:19][C:18]=3[C:12]3[NH:11][C:10]([NH:9][C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])=[N:14][C:13]=3[CH:15]=2)=[O:26])=[CH:57][CH:56]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78074-BromoanilineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422813HCID 178422813, compound

Product 1

HCID 178422740HCID 178422740, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(2,6-dichlorophenyl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-6, 0.080 g, 0.204 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.130 g, 0.400 mmol), TEA (1.5 mL), DMF (1.5 mL), THF (7.0 mL) and 4-bromo aniline (0.070 g, 0.400 mmol) to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 1.30-1.45 (m, 3H), 1.46-1.56 (m, 3H), 3.08 (s, 2H), 7.39 (m, 2H), 7.53 (d, J=8.7 Hz, 4H), 7.68 (d, J=8.7 Hz, 2H), 9.78 (s, 1H), 11.50-12.00 (s, 2H); MS [M+H]+: 547.16.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-89f8ec5c0b064f049b91d55cadfae11f
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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