1-[2-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propyl}oxy)pyridin-4-yl]methanamine → 6-cyano-4-oxo-N-[[3-(1H-1,2,4-triazol-5-ylmethoxymethyl)phenyl]methyl]-1H-quinazoline-2-carboxamide

HRID 606389Notes

Reaction equation

HRID 606389 reaction equation
O=C1C2C(=CC=CC=2)N=C(C(OCC)=O)N1.[C:17]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[C:24]([C:29]([O:31]CC)=O)[NH:23][C:22]2=[O:34])#[N:18].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)N2C=NC(CCCOC3C=C(CN)C=CN=3)=N2)C=CC=CC=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:78]2[CH:82]=[N:81][C:80]([CH2:83][O:84][CH2:85][C:86]3[CH:87]=[C:88]([CH2:92][NH2:93])[CH:89]=[CH:90][CH:91]=3)=[N:79]2)C=CC=CC=1>>[C:17]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[N:25]=[C:24]([C:29]([NH:93][CH2:92][C:88]1[CH:89]=[CH:90][CH:91]=[C:86]([CH2:85][O:84][CH2:83][C:80]3[N:81]=[CH:82][NH:78][N:79]=3)[CH:87]=1)=[O:31])[NH:23][C:22]2=[O:34])#[N:18]

Participants

5

Reactant 4

HCID 667687691-[2-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propyl}oxy)pyridin-4-yl]methanamineHCID 667691011-{3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methyl}oxy)methyl]phenyl}methanamineHCID 135437466Ethyl 4-oxo-3,4-dihydroquinazoline-2-carboxylateHCID 136054489Ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 1785094966-cyano-4-oxo-N-[[3-(1H-1,2,4-triazol-5-ylmethoxymethyl)phenyl]methyl]-1H-quinazoline-2-carboxamide

Procedure

By a method similar to that in Example 22, and using, instead of ethyl 4-oxo-3,4-dihydro-2-quinazolinecarboxylate, ethyl 6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxylate obtained in Reference Example 51 and using, instead of 1-[2-({3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propyl}oxy)pyridin-4-yl]methaneamine, 1-{3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methyl}oxy)methyl]phenyl}methanamine obtained in Reference Example 38, the title compound was obtained as a white powder (20 mg, 6%).

Workup

  1. customobtained in Reference Example 51
  2. customobtained in Reference Example 38

Sources & evidence

ORD record
ord-96196a44d6b243d7a712699bb14ca2fa
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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