Ethanolamine → HCID 118497101, compound

HRID 522090Notes

Reaction equation

HRID 522090 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18](OCC)=[O:19])[CH:8]=1)=[O:5].[CH2:34]([CH2:36][NH2:37])[OH:35].C(N(CC)C(C)C)(C)C>CO>[Cl:1][C:2]1[CH:26]=[CH:25][C:24]([C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=[C:9]([C:18]([NH:37][CH2:36][CH2:34][OH:35])=[O:19])[CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 118497028HCID 118497028, compound

Product 1

HCID 118497101HCID 118497101, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 5-(2-chloro-5-(3-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylate (Example 113, 40 mg, 0.09 mmol), ethanolamine (15.7 mg, 0.26 mmol) and N,N-diisopropylethylamine (33.3 mg, 0.26 mmol) in methanol (1 mL) was heated at 50° C. in a sealed vial for 17 hours. The reaction was cooled and purified using reverse phase column chromatography eluting with 3-50% MeCN in water with 0.1% ammonia to afford the title compound as a white solid (18 mg, 44%).

Workup

  1. temperatureThe reaction was cooled
  2. custompurified
  3. washeluting with 3-50% MeCN in water with 0.1% ammonia

Sources & evidence

ORD record
ord-5ae5a68671614135b95b67478b0577e6
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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