Ethanolamine → 5-{[2-chloro-4-fluoro-5-(pyridin-2-yl)benzoyl]amino}-N-(2-hydroxyethyl)-1-phenyl-1H-Pyrazole-3-carboxamide

HRID 522122Notes

Reaction equation

[B-](F)(F)(F)F.CN(C(ON1C(=O)C=CC=C1)=[N+](C)C)C.[Cl:21][C:22]1[CH:44]=[C:43]([F:45])[C:42]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=2)=[CH:41][C:23]=1[C:24]([NH:26][C:27]1[N:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:30]=[C:29]([C:38]([OH:40])=O)[CH:28]=1)=[O:25].C(N(CC)C(C)C)(C)C.[CH2:61]([CH2:63][NH2:64])[OH:62]>CN(C=O)C>[Cl:21][C:22]1[CH:44]=[C:43]([F:45])[C:42]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=2)=[CH:41][C:23]=1[C:24]([NH:26][C:27]1[N:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:30]=[C:29]([C:38]([NH:64][CH2:63][CH2:61][OH:62])=[O:40])[CH:28]=1)=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

TPTU (510 mg, 1.72 mmol) and 5-(2-chloro-4-fluoro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 108, 500 mg, 1.14 mmol) were dissolved in DMF (2.5 mL) at 0° C. N,N-diisopropylethylamine (0.6 mL, 3.43 mmol) was then added and the mixture stirred at 0° C. for 15 minutes. Ethanolamine (99.5 mL, 1.65 mmol) was then added and the mixture stirred at room temperature for 2 hours. The solvent was removed in vacuo and the resulting brown solid triturated with dichloromethane/TBME/heptane (4:2:0.5, 5 mL) to give a white solid, which was further triturated with MeOH (5 mL) to afford the title compound as a white solid (262 mg, 48%).

Workup

stirringthe mixture stirred at room temperature for 2 hours
customThe solvent was removed in vacuo
customthe resulting brown solid triturated with dichloromethane/TBME/heptane (4:2:0.5, 5 mL)
customto give a white solid, which
customwas further triturated with MeOH (5 mL)

Sources & evidence

ORD record: ord-3bede5d99d7e4fa784932575c2367045
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328096B2

Reaction notes

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