Propylamine → HCID 69136081, compound

HRID 969493Notes

Reaction equation

HRID 969493 reaction equation
[CH3:1][C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[C:9]([C:22]([OH:24])=O)[C:10]3[CH2:11][CH2:12][CH:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[O:14][C:15]=3[C:4]=2[N:3]=1.F[B-](F)(F)F.[N:30]1(OC(N(C)C)=[N+](C)C)[C:34]2C=CC=[CH:38][C:33]=2N=N1.C(N(CC)CC)C.C(N)CC>CN(C)C=O.O>[CH2:34]([NH:30][C:22]([C:9]1[C:10]2[CH2:11][CH2:12][CH:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:14][C:15]=2[C:4]2[N:3]=[C:2]([CH3:1])[N:6]([CH3:7])[C:5]=2[CH:8]=1)=[O:24])[CH2:33][CH3:38]

Participants

7

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69134413HCID 69134413, compound

Product 1

HCID 69136081HCID 69136081, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.3 g (0.93 mmol) 2,3-dimethyl-8-phenyl-3,6,7,8-tetrahydro-chromeno[7,8-d]imidazole-5-carboxylic acid and 0.3 g (0.93 mmol) O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) in dimethylformamide (5 ml) were added 240 μl (1.9 mmol) triethylamine and 76 μl (0.93 mmol) propylamine and the suspension was stirred overnight at room temperature. The reaction was poured into water, the precipitate filtered off and purified by column chromatography on silica gel (dichloromethane/methanol=50:1) to afford 154 mg (46%) of the toe compound as a white powder.

Workup

  1. filtrationthe precipitate filtered off
  2. custompurified by column chromatography on silica gel (dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-fa34bc935b734e4da0930d69aecfa535
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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