4-Methylmorpholine → HCID 178446462, compound

HRID 1898359Notes

Reaction equation

HRID 1898359 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=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.[N:32]1(OC(N(C)C)=[N+](C)C)[C:36]2C=[CH:38][CH:39]=[CH:40][C:35]=2N=N1.CN1CCOCC1.C(N)CCCC>C1COCC1.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:26])[C:7]=1[NH:8][C:9]1[NH:10][C:11]2[C:17]3[CH2:18][C:19]([CH3:21])([CH3:22])[O:20][C:16]=3[C:15]([C:23]([NH:32][CH2:36][CH2:35][CH2:40][CH2:39][CH3:38])=[O:24])=[CH:14][C:12]=2[N:13]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 8060PentylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178422814HCID 178422814, compound

Product 1

HCID 178446462HCID 178446462, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared following the procedure as described for Example-1 using 2-[(3,5-dichloropyridin-4-yl)amino]-7,7-dimethyl-7,8-dihydro-1H-furo[3,2-e]benzimidazole-5-carboxylic acid (Intermediate-3, 0.050 g, 0.127 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.082 g, 0.225 mmol), N-methyl morpholine (0.5 mL), DMF (1.0 mL), THF (5.0 mL) and n-pentyl amine (0.022 g, 0.254 mmol) to afford 0.012 g of the desired product. 1HNMR (DMSO-d6): δ 1.29 (t, J=6.3 Hz, 3H), 1.64 (s, 3H), 1.71 (s, 6H), 1.91 (s, 3H), 3.42 (s, 2H), 3.68-3.74 (m, 2H), 7.62 (s, 1H), 8.10 (m, 1H), 8.84 (s, 2H), 11.23 (s, 1H), 11.81 (s, 1H); MS [M+H]+: 462.43.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e9d0540dcdc04d4eab4b542d8e1c10c4
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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