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Water → HCID 178433907, compound

HRID 2236787
Notes
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Reaction equation

HRID 2236787 reaction equation
[Cl:1][C:2]1[C:3]([CH3:15])=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[C:6]=1[CH3:7].[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][C:21](=[O:28])[C:20]2=[CH:29]OC.CCOC(C)=O.O>CN(C)C=O>[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][C:21](=[O:28])[C:20]2=[CH:29][NH:14][C:11]1[CH:12]=[CH:13][C:8]([N:5]2[C:6]([CH3:7])=[C:2]([Cl:1])[C:3]([CH3:15])=[N:4]2)=[CH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 196165864-(4-CHLORO-3,5-DIMETHYL-1H-PYRAZOL-1-YL)ANILINEHCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Product 1

HCID 178433907HCID 178433907, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

The 4-(4-Chloro-3,5-dimethyl-pyrazol-1-yl)-phenylamine (130 mg, 0.58 mmol) and 6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione (120 mg, 0.43 mmol) is heated in N,N-dimethylformamide (10 mL) at 100° C. for 4 h. EtOAc (100 mL) and H2O (20 mL) is then added. The EtOAc layer is washed with H2O (3×20 mL) and brine (15 mL) and dried over MgSO4. Upon removal of EtOAc, precipitate formed and the precipitate is collected and washed with MeOH and Et2O and dried to provide the title compound (64 mg, 32%). 1H NMR (400 MHz, DMSO) δ 12.56(1H, d, J=12.4 Hz), 11.46 (1H, s), 8.98 (1H, d, J=12.4 Hz), 8.50 (1H, s), 7.43-7.94 (6H, m), 2.30 (3H, s), 2.21 (3H, s); MP: 290-291° C.; Anal. Cacl. for C21H16BrClN4O2: C, 53.47; H, 3.42; N, 11.88. Found: C, 51.49; H, 2.94; N, 11.31.

Workup

  1. washThe EtOAc layer is washed with H2O (3×20 mL) and brine (15 mL)
  2. dry with materialdried over MgSO4
  3. customUpon removal of EtOAc, precipitate
  4. customformed
  5. customthe precipitate is collected
  6. washwashed with MeOH and Et2O
  7. customdried

Sources & evidence

ORD record
ord-e04c9d4b0ccb4f169cb9d23ac780e422
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07713994B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes