Tetrahydrofuran → HCID 178422226, compound

HRID 1898375Notes

Reaction equation

HRID 1898375 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.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C1COCC1.[F:53][C:54]1[CH:61]=[CH:60][C:57]([CH2:58][NH2:59])=[CH:56][CH:55]=1>CN(C=O)C>[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]([NH:59][CH2:58][C:57]3[CH:60]=[CH:61][C:54]([F:53])=[CH:55][CH:56]=3)=[O:23])=[CH:14][C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 673264-FluorobenzylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422230HCID 178422230, compound

Product 1

HCID 178422226HCID 178422226, compoundYield 19.5%

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, 0.060 g, 0.159 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.102 g, 0.318 mmol), TEA (0.032 g, 0.318 mmol), THF (5.0 mL), DMF (1.0 mL), 4-fluoro benzyl amine (0.035 g, 0.318 mmol) to afford 0.015 g of the desired product. 1HNMR (DMSO-d6): δ 2.49 (s, 3H), 4.55 (d, J=5.4 Hz, 2H), 6.22 (s, 1H), 7.13-7.16 (m, 2H), 7.41 (m, 3H), 8.44 (s, 2H), 8.61 (s, 1H), 11.22 (s, 1H), 11.76 (s, 1H); MS [M+H]+: 484.24.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-10761c76a876465ca147d23717ce93b4
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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