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2-Aminopropanol → 2'-Fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4'-methyl-biphenyl-3-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide

HRID 2091821
Notes
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Reaction equation

HRID 2091821 reaction equation
CCN=C=NCCCN(C)C.[F:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[C:20]1[CH:25]=[C:24]([C:26]2[N:27]([CH:31]([CH3:33])[CH3:32])[N:28]=[CH:29][CH:30]=2)[CH:23]=[C:22]([C:34](O)=[O:35])[CH:21]=1.C1C=CC2N(O)N=NC=2C=1.CN1C(=O)CCC1.[NH2:54][CH:55]([CH3:58])[CH2:56][OH:57]>C(Cl)Cl>[OH:57][CH2:56][CH:55]([NH:54][C:34]([C:22]1[CH:21]=[C:20]([C:14]2[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=2[F:12])[CH:25]=[C:24]([C:26]2[N:27]([CH:31]([CH3:33])[CH3:32])[N:28]=[CH:29][CH:30]=2)[CH:23]=1)=[O:35])[CH3:58]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 51262-AminopropanolHCID 13387N-methyl-2-pyrrolidoneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 577705982'-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4'-methyl-biphenyl-3-carboxylic acid

Product 1

HCID 57770677
2'-Fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4'-methyl-biphenyl-3-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide
Yield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

EDCI (54.0 mg, 0.282 mmol) was added in one portion to a solution of 2′-fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4′-methyl-biphenyl-3-carboxylic acid (77.4 mg, 0.229 mmol), HOBt (40.0 mg, 0.296 mmol) and NMP (101.5 mg, 1.000 mmol) in CH2Cl2 (5 mL) at 0° C. After the reaction stirred at the same temperature for 1 hour, 2-amino-propan-1-ol (54 mg, 0.72 mmol) was added. The mixture was allowed to warm to room temperature and was stirred overnight. Solvent was removed under reduced pressure and the residue was purified by column chromatography to afford 2′-Fluoro-5-(2-isopropyl-2H-pyrazol-3-yl)-4′-methyl-biphenyl-3-carboxylic acid (2-hydroxy-1-methyl-ethyl)-amide as white solid (54 mg, 46%). MS (N+H)=396.

Workup

  1. stirringwas stirred overnight
  2. customSolvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-27681f779edc4f9982422cace4e042eb
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440673B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes