1-trityl-1H-[1,2,4]triazole-3-carboxylic acid → 5-methyl-4-oxo-N-{[3-({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]carbonyl}amino)phenyl]methyl}-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

HRID 606397Notes

Reaction equation

HRID 606397 reaction equation
NC1C=C(CNC(C2NC(=O)C3C(=CC=C(C#N)C=3)N=2)=O)C=CC=1.[NH2:25][C:26]1[CH:27]=[C:28]([CH2:32][NH:33][C:34]([C:36]2[NH:37][C:38](=[O:46])[C:39]3[C:44]([CH3:45])=[CH:43][S:42][C:40]=3[N:41]=2)=[O:35])[CH:29]=[CH:30][CH:31]=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)N2C=NC(CCC(O)=O)=N2)C=CC=CC=1.[C:76]1([C:82]([C:97]2[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=2)([C:91]2[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=2)[N:83]2[CH:87]=[N:86][C:85]([C:88](O)=[O:89])=[N:84]2)[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1>>[CH3:45][C:44]1[C:39]2[C:38](=[O:46])[NH:37][C:36]([C:34]([NH:33][CH2:32][C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([NH:25][C:88]([C:85]4[N:86]=[CH:87][N:83]([C:82]([C:76]5[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=5)([C:91]5[CH:92]=[CH:93][CH:94]=[CH:95][CH:96]=5)[C:97]5[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=5)[N:84]=4)=[O:89])[CH:27]=3)=[O:35])=[N:41][C:40]=2[S:42][CH:43]=1

Participants

5

Reactant 4

HCID 218918071-trityl-1H-[1,2,4]triazole-3-carboxylic acidHCID 57708760N-[(3-aminophenyl)methyl]-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamideHCID 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 667691025-methyl-4-oxo-N-{[3-({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]carbonyl}amino)phenyl]methyl}-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

Procedure

By a method similar to that in Step 1 of Example 32, and using, instead of N-[(3-aminophenyl)methyl]-6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxamide, N-[(3-aminophenyl)methyl]-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide obtained in Reference Example 48 and using, instead of 3-[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]propanoic acid, 1-(triphenylmethyl)-1H-1,2,4-triazole-3-carboxylic acid obtained in Reference Example 35, 5-methyl-4-oxo-N-{[3-({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]carbonyl}amino)phenyl]methyl}-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide was obtained as a white powder (575 mg, 88%).

Workup

  1. customobtained in Reference Example 48
  2. customobtained in Reference Example 35

Sources & evidence

ORD record
ord-90b5860ce3cc483da521905ce34f766a
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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