Pyridine → HCID 135674996, compound

HRID 1198193Notes

Reaction equation

HRID 1198193 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([C:18]3[CH:35]=[CH:34][C:21]([C:22]([NH:24][CH2:25][CH:26]([OH:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[O:23])=[CH:20][CH:19]=3)[CH2:15][C:16]#[CH:17])[CH:8]=2)[N:3]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37].N1C=CC=CC=1>CN(C=O)C>[C:36]([O:33][CH:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:25][NH:24][C:22](=[O:23])[C:21]1[CH:20]=[CH:19][C:18]([N:14]([CH2:13][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([CH3:1])[NH:11][C:10]3=[O:12])[CH2:15][C:16]#[CH:17])=[CH:35][CH:34]=1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 135674983HCID 135674983, compound

Product 1

HCID 135674996HCID 135674996, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

p-[N-(2-Methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]-N-(2-hydroxy-2-phenylethyl)benzamide (0.105 g) was dissolved in DMF (3 ml) and acetic anhydride (34 mg) and pyridine (37 mg) were added in turn. The mixture was stirred at 20° C. for 24 hours. The mixture was evaporated and the residue was triturated with water (5 ml). The solid was filtered off, washed with water and dried in air to give N-(2-acetoxy-2-phenylethyl)-p-[N-(2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]benzamide (0.095 g; containing 1 equivalent of water), m.p. 203°-205° C.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was triturated with water (5 ml)
  3. filtrationThe solid was filtered off
  4. washwashed with water
  5. customdried in air

Sources & evidence

ORD record
ord-31673c9af5d640508e29cfebb6604ab6
Source dataset
uspto-grants-1994_01
Patent number
US05280027

Reaction notes

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