Ethanolamine → HCID 58989886, compound

HRID 1663157Notes

Reaction equation

HRID 1663157 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:29])=[C:24]([CH:28]=1)[C:25](O)=[O:26])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.[NH2:41][CH2:42][CH2:43][OH:44].CN1CCOCC1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C>[CH2:1]([O:8][NH:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:29])=[C:24]([CH:28]=1)[C:25]([NH:41][CH2:42][CH2:43][OH:44])=[O:26])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 700EthanolamineHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 58989938HCID 58989938, compound

Product 1

HCID 58989886HCID 58989886, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[(2-Benzyloxycarbamoyl-phenylamino)-methyl]-2-fluoro-benzoic acid (Example 498, 96.5 mg) and 1-hydroxybenzotriazole hydrate (36 mg) was dissolved in DMF (1.0 ml). 2-Amino-ethanol (15 μl), N-methylmorpholine (28 μl), and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (50.1 mg) was added in that order. The reaction mixture was shaken at room temperature for 15 hours. The solvent was evaporated under reduced pressure and the residue was dissolved in dichloromethane and evaporated onto silica gel. Purification by column chromatography on silica gel (elution with 50-100% EtOAc in petroleum ether) gave the title compound.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customevaporated onto silica gel
  4. customPurification by column chromatography on silica gel (elution with 50-100% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c7b7fe16814648638ef1b58c748fb94d
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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