1-Hydroxybenzotriazole → 6-cyano-4-oxo-N-{[3-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propanoyl}amino)phenyl]methyl}-3,4-dihydroquinazoline-2-carboxamide

HRID 606390Notes

Reaction equation

HRID 606390 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][NH:9][C:10]([C:12]2[NH:21][C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:23]#[N:24])[CH:18]=3)[N:13]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.[C:25]1([C:31]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:32]2[CH:36]=[N:35][C:34]([CH2:37][CH2:38][C:39](O)=[O:40])=[N:33]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[C:23]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:10]([NH:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:39](=[O:40])[CH2:38][CH2:37][C:34]3[N:35]=[CH:36][N:32]([C:31]([C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[N:33]=3)[CH:3]=1)=[O:11])[NH:21][C:20]2=[O:22])#[N:24]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667689233-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propanoic acidHCID 136054507N-[(3-aminophenyl)methyl]-6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxamide

Product 1

HCID 1363809646-cyano-4-oxo-N-{[3-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propanoyl}amino)phenyl]methyl}-3,4-dihydroquinazoline-2-carboxamideYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of N-[(3-aminophenyl)methyl]-6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxamide obtained in Reference Example 45 (120 mg, 0.376 mmol), 3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propanoic acid obtained in Reference Example 25 (152 mg, 0.396 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl-carbodiimide hydrochloride (106 mg, 0.554 mmol) and 1-hydroxybenzotriazole (74.9 mg, 0.554 mmol) in DMF (5 mL) was stirred at 40° C. for 15 hr. The reaction mixture was concentrated under reduced pressure, and water was added to residue. The resulting solid was collected by filtration, washed with water and IPE, and dried to give 6-cyano-4-oxo-N-{[3-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propanoyl}amino)phenyl]methyl}-3,4-dihydroquinazoline-2-carboxamide as a white powder (232.0 mg, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  2. additionwas added to residue
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water and IPE
  5. customdried

Sources & evidence

ORD record
ord-05174b726f114c228e049004d3e0d140
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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