Ethanolamine → HCID 86607439, compound

HRID 969485Notes

Reaction equation

HRID 969485 reaction equation
[CH3:1][C:2]1[N:6]([CH3:7])[C:5]2[CH:8]=[C:9]([C:22](O)=[O:23])[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.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[CH2:47]([CH2:49][NH2:50])[OH:48].O>ClCCl>[OH:48][CH2:47][CH2:49][NH:50][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:23]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69134413HCID 69134413, compound

Product 1

HCID 86607439HCID 86607439, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension 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 in dichloromethane (9 ml) were added 0.45 g (1.4 mmol) O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU) and the suspension was stirred for 64 h at room temperature. 284 μl (4.7 mmol) Ethanolamine were added and the mixture was stirred for 24 h at room temperature. The reaction was poured into water and the precipitate filtered off. The residue was purified by chromatography on silica gel (dichloromethane/methanol=15:1) to afford 53 mg (17%) of the title compound as a yellow solid. m.p. 228°-229° C.

Workup

  1. stirringthe mixture was stirred for 24 h at room temperature
  2. filtrationthe precipitate filtered off
  3. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol=15:1)

Sources & evidence

ORD record
ord-4fa37e60a46e404fa7c26c55f981cf84
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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