Ethanolamine → HCID 69735253, compound

HRID 496451Notes

Reaction equation

HRID 496451 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[N:13]1([CH2:18][C@@H:19]([O:26][C:27]2[CH:36]=[CH:35][C:34]3[C:33](=[O:37])[CH2:32][CH2:31][CH2:30][C:29]=3[C:28]=2[CH2:38][S:39][C:40]2[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=2)[C:43](O)=[O:44])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:17]=[CH:16][N:15]=[CH:14]1.[NH2:49][CH2:50][CH2:51][OH:52]>O>[OH:52][CH2:51][CH2:50][NH:49][C:43](=[O:44])[C:42]1[CH:46]=[CH:47][CH:48]=[C:40]([S:39][CH2:38][C:28]2[C:29]3[CH2:30][CH2:31][CH2:32][C:33](=[O:37])[C:34]=3[CH:35]=[CH:36][C:27]=2[O:26][C@@H:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[CH:41]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 60029928HCID 60029928, compound

Product 1

HCID 69735253HCID 69735253, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,1′-carbonyldiimidazole (49 mg, 0.30 mmol, 0.60M in DMF) and 3-{[(2-{[(1S)-2-(1H-imidazol-1-yl)-1-phenylethyl]oxy}-5-oxo-5,6,7,8-tetrahydro-1-naphthalenyl)methyl]sulfanyl}benzoic acid (50 mg, 0.10 mmol, 0.20M in DMF) in a capped vial were placed in a heater-shaker at 55° C. for 20 min. It was removed from the heater-shaker and stood at room temperature. A solution of 2-aminoethanol (31 mg, 0.50 mmol, 1.0M in DMF) was added and the reaction mixture was further shaken at room temperature over-night. Water (6 ml) was added and the mixture was shaken at room temperature for 10 min. before being stored in refrigerator over-night. The precipitate was filtered, washed with cold water (2×0.5 ml) and dried in a vacuum oven at 40° C. until constant weight was obtained. 44 mg of the required benzamide was obtained as a beige solid: Low resolution mass spectrum (LC-MS, APCI) m/z 542 [M+H]+.

Workup

  1. customIt was removed from the heater-shaker
  2. customstood at room temperature
  3. stirringthe mixture was shaken at room temperature for 10 min.
  4. filtrationThe precipitate was filtered
  5. washwashed with cold water (2×0.5 ml)
  6. customdried in a vacuum oven at 40° C. until constant weight
  7. customwas obtained

Sources & evidence

ORD record
ord-732c5ec67eed4baebbbdb9d9c33a1408
Source dataset
uspto-grants-2005_09
Patent number
US06943183B2

Reaction notes

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