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)methyl]phenyl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

HRID 606394Notes

Reaction equation

HRID 606394 reaction equation
Cl.NCC1C=C(CNC(C2NC(=O)C3C(=CC=C(C#N)C=3)N=2)=O)C=CC=1.Cl.[NH2:28][CH2:29][C:30]1[CH:31]=[C:32]([CH2:36][NH:37][C:38]([C:40]2[NH:41][C:42](=[O:50])[C:43]3[C:48]([CH3:49])=[CH:47][S:46][C:44]=3[N:45]=2)=[O:39])[CH:33]=[CH:34][CH:35]=1.N1C=NC(CC(O)=O)=N1.[C:60]1([C:66]([C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)([C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[N:67]2[CH:71]=[N:70][C:69]([C:72](O)=[O:73])=[N:68]2)[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>>[CH3:49][C:48]1[C:43]2[C:42](=[O:50])[NH:41][C:40]([C:38]([NH:37][CH2:36][C:32]3[CH:33]=[CH:34][CH:35]=[C:30]([CH2:29][NH:28][C:72]([C:69]4[N:70]=[CH:71][N:67]([C:66]([C:60]5[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=5)([C:75]5[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=5)[C:81]5[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=5)[N:68]=4)=[O:73])[CH:31]=3)=[O:39])=[N:45][C:44]=2[S:46][CH:47]=1

Participants

5

Reactant 4

HCID 218918071-trityl-1H-[1,2,4]triazole-3-carboxylic acidHCID 66769185N-{[3-(aminomethyl)phenyl]methyl}-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide hydrochlorideHCID 136380963N-{[3-(aminomethyl)phenyl]methyl}-6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxamide hydrochlorideHCID 1785252442-(1H-1,2,4-triazol-3-yl)acetic acid

Product 1

HCID 667692035-methyl-4-oxo-N-({3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]carbonyl}amino)methyl]phenyl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

Procedure

By a method similar to that in Example 34, and using, instead of N-{[3-(aminomethyl)phenyl]methyl}-6-cyano-4-oxo-3,4-dihydroquinazoline-2-carboxamide hydrochloride, N-{[3-(aminomethyl)phenyl]methyl}-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide hydrochloride obtained in Reference Example 50 and using, instead of 1H-1,2,4-triazol-3-ylacetic 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)methyl]phenyl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide was obtained as a white powder (597 mg, 90%).

Workup

  1. customobtained in Reference Example 50
  2. customobtained in Reference Example 35

Sources & evidence

ORD record
ord-1063248b129647c38291a572d032cf2e
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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