Diisopropylethylamine → HCID 178481739, compound

HRID 1685137Notes

Reaction equation

HRID 1685137 reaction equation
COC1C=CC(C[O:8][C:9]2[C:10]([C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][C:25]4=[O:30])=[CH:20][CH:19]=3)=[N:11][N:12]([CH3:17])[C:13]=2[C:14](O)=O)=CC=1.[NH2:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][C:41]=1[NH2:42])[C:37]#[N:38].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[OH:8][C:9]1[C:10]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C:25]3=[O:30])=[CH:20][CH:19]=2)=[N:11][N:12]([CH3:17])[C:13]=1[C:14]1[NH:42][C:41]2[CH:40]=[CH:39][C:36]([C:37]#[N:38])=[CH:35][C:34]=2[N:33]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 7372853,4-DiaminobenzonitrileHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68052781HCID 68052781, compound

Product 1

HCID 178481739HCID 178481739, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-methoxybenzyloxy)-1-methyl-3-(4-(2-oxopiperidin-1-yl)phenyl)-1H-pyrazole-5-carboxylic acid T-22 (180 mg, 0.42 mmol) in N,N-dimethylformamide (4 mL) were added 3,4-diaminobenzonitrile (66 mg, 0.5 mmol), HATU (204 mg, 0.54 mmol) and diisopropylethylamine (0.22 mL, 1.3 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated brine. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure. The residue was purified by flash chromatography. To the purified fraction (155 mg, 0.28 mmol) was added acetic acid (4 mL). The reaction mixture was heated in a microwave reactor at 150° C. for 55 minutes. Solvent was evaporated under reduced pressure. To the residue was added trifluoroacetic acid (4 mL). The reaction mixture was heated in a microwave reactor at 120° C. for 30 minutes. Solvent was evaporated under reduced pressure. The crude product was purified by flash chromatography to afford the desired 2-(4-hydroxy-1-methyl-3-(4-(2-oxopiperidin-1-yl)phenyl)-1H-pyrazol-5-yl)-1H-benzo[d]imidazole-5-carbonitrile T-23 (110 mg, 0.27 mmol).

Workup

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customSolvent was evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography
  5. additionTo the purified fraction (155 mg, 0.28 mmol) was added acetic acid (4 mL)
  6. temperatureThe reaction mixture was heated in a microwave reactor at 150° C. for 55 minutes
  7. customSolvent was evaporated under reduced pressure
  8. additionTo the residue was added trifluoroacetic acid (4 mL)
  9. temperatureThe reaction mixture was heated in a microwave reactor at 120° C. for 30 minutes
  10. customSolvent was evaporated under reduced pressure
  11. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-08d8017c27d14b979b41f4d598e383dd
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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