Ammonia → HCID 135675007, compound

HRID 1198194Notes

Reaction equation

HRID 1198194 reaction equation
NC(C)(CC1C=CC=CC=1)C#N.[C:13]([C:15]([NH:24][C:25](=[O:57])[C:26]1[CH:31]=[CH:30][C:29]([N:32]([CH2:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[N:43]=[C:42]([CH3:47])[N:41](COC(=O)C(C)(C)C)[C:40]3=[O:56])[CH2:33][C:34]#[CH:35])=[CH:28][CH:27]=1)([CH3:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)#[N:14].N>CO>[C:13]([C:15]([NH:24][C:25](=[O:57])[C:26]1[CH:31]=[CH:30][C:29]([N:32]([CH2:36][C:37]2[CH:38]=[C:39]3[C:44](=[CH:45][CH:46]=2)[N:43]=[C:42]([CH3:47])[NH:41][C:40]3=[O:56])[CH2:33][C:34]#[CH:35])=[CH:28][CH:27]=1)([CH3:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)#[N:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 13363602HCID 13363602, compoundHCID 19104054HCID 19104054, compound

Product 1

HCID 135675007HCID 135675007, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The process described in Example 1 was repeated except that (R/S)-2-amino-2-methyl-3-phenylpropiononitrile (Eur. J. Med. Chem. Clin. Ther., 1975, 10, 117) was used in place of (-)-(2R)-2-amino-2-phenylethanol and that the N-(2-cyano-1-phenylprop-2-yl)-p-[N-(2-methyl-4-oxo-3-(pivaloyloxymethyl)-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]benzamide so produced was dissolved in methanol which had been saturated with ammonia gas and the mixture was stirred at laboratory temperature for 24 hours. The mixture was evaporated to give N-(2-cyano-1-phenylprop-2-yl)-p-[N-(2-methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl)-N-(prop-2-ynyl)amino]benzamide, m.p. 208°-209° C.

Workup

  1. customso produced
  2. customThe mixture was evaporated

Sources & evidence

ORD record
ord-11bd092bc40c40aea9d1d73d3c0cd766
Source dataset
uspto-grants-1994_01
Patent number
US05280027

Reaction notes

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