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Dimethylformamide → N-(3-fluoro-4-(isoquinolin-5-yl)phenyl)-1-((S)-2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 2356354
Notes
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Reaction equation

HRID 2356354 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:18])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[CH:13]2.[OH:19][C@@H:20]([CH3:38])[CH2:21][N:22]1[C:26]([CH3:27])=[C:25]([C:28](O)=[O:29])[C:24](=[O:31])[N:23]1[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CN(C=O)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:28]([C:25]2[C:24](=[O:31])[N:23]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:22]([CH2:21][C@@H:20]([OH:19])[CH3:38])[C:26]=2[CH3:27])=[O:29])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][N:12]=[CH:13]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 59383933(S)-1-(2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acidHCID 593839363-Fluoro-4-(isoquinolin-5-yl)benzenamine

Product 1

HCID 24998657N-(3-fluoro-4-(isoquinolin-5-yl)phenyl)-1-((S)-2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 33,435.801%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-fluoro-4-(isoquinolin-5-yl)benzenamine (309.9 mg, 1301 μmol) and (S)-1-(2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (359 mg, 1301 μmol) were suspended in DCM (6.5 ml) and DMF (0.65 ml) and hatu (579 mg, 1523 μmol) was added. The reaction was stirred under nitrogen for 5 days, and then filtered. The solid was washed with DCM, and the filtrate was concentrated and purified on silica gel (50:1->40:1->30:1->10:1 DCM/MeOH. The fractions with product were collected, concentrated, treated with MeOH and filtered. The solid was washed with MeOH, collected, and dried under high vacuum to afford the desired N-(3-fluoro-4-(isoquinolin-5-yl)phenyl)-1-((S)-2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (216.0 mg, 435.0 mmol, 33% yield). MS (ESI pos. ion) m/z: 497 (MH+). Calc'd exact mass for C29H25FN4O3: 496. 1H NMR (400 MHz, CDCl3) δ 10.93 (s, 1H), 9.30 (s, 1H), 8.49 (d, J=6.0 Hz, 1H), 8.01 (dd, J=7.0 Hz, 3.0 Hz, 1H), 7.87 (dd, J=12.0 Hz, 2.0 Hz, 1H), 7.71-7.64 (m, 2H), 7.59-7.52 (m, 3H), 7.48 (d, J=8.0 Hz, 1H), 7.42-7.34 (m, 3H), 7.31 (d, J=8.0 Hz, 1H), 4.00-3.83 (m, 2H), 3.72 (dd, J=15.0 Hz, 3.0 Hz, 1H), 2.89 (s, 3H), 1.29-1.24 (m, 1H), 1.11 (d, J=6.0 Hz, 3H).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with DCM
  3. concentrationthe filtrate was concentrated
  4. custompurified on silica gel (50:1->40:1->30:1->10:1 DCM/MeOH
  5. customThe fractions with product were collected
  6. concentrationconcentrated
  7. additiontreated with MeOH
  8. filtrationfiltered
  9. washThe solid was washed with MeOH
  10. customcollected
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-1c20ac1f86b14ccfa7df876941396078
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759344B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes