Water → HCID 86607441, compound

HRID 969494Notes

Reaction equation

HRID 969494 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.C(N(CC)CC)C.[NH2:32][CH2:33][CH:34]([OH:37])[CH2:35][OH:36].O>CN(C)C=O>[OH:37][CH:34]([CH2:35][OH:36])[CH2:33][NH:32][C:22]([C:9]1[C:10]2[CH2:11][CH2:12][CH:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 735613-Amino-1,2-propanediolHCID 69134413HCID 69134413, compound

Product 1

HCID 86607441HCID 86607441, compoundYield 270%

Reagents, catalysts & solvents 1

HCID 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 tetrafluoro-borate (TBTU) in dimethylformamide (5 ml) were added 240 μl (1.9 mmol) triethylamine and 71 μl (0.93 mmol) 3-amino-propane-1,2-diol 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=8:1) to afford 100 mg (270%) of the title compound as a white solid.

Workup

  1. filtrationthe precipitate filtered off
  2. custompurified by column chromatography on silica gel (dichloromethane/methanol=8:1)

Sources & evidence

ORD record
ord-9e0106e9486341699f2ac9adb32f7bba
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

Loading…