Acetic Anhydride → HCID 59333752, compound

HRID 1930721Notes

Reaction equation

HRID 1930721 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:17]=[C:18]([CH2:26][CH2:27][CH:28]3[CH2:32][CH2:31][CH2:30][O:29]3)[C:19]3[CH2:25][NH:24][CH2:23][CH2:22][C:20]=3[N:21]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:17]=[C:18]([CH2:26][CH2:27][CH:28]3[CH2:32][CH2:31][CH2:30][O:29]3)[C:19]3[CH2:25][N:24]([C:33](=[O:35])[CH3:34])[CH2:23][CH2:22][C:20]=3[N:21]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 59333810HCID 59333810, compound

Product 1

HCID 59333752HCID 59333752, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N -(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4-(2-(tetrahydrofuran-2-yl)ethyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.114 g, 0.26 mmol) in dichloromethane (2 mL) was added acetic anhydride (0.027 mL, 0.29 mmol) at rt. The reaction mixture was stirred for 45 minutes. The solvent was concentrated; the residue was suspended with methanol and purified by prepHPLC. Fractions were pooled and the solvent was evaporated. The residue was dissolved in water/acetonitrile-mixture (50:50) and freezedried giving 1-(2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(2-(tetrahydrofuran-2-yl)ethyl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanone (0.062 g, 49.6%).

Workup

  1. concentrationThe solvent was concentrated
  2. custompurified by prepHPLC
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in water/acetonitrile-mixture (50:50)
  5. customfreezedried

Sources & evidence

ORD record
ord-2f74a398efb345669a40d34b53dab951
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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