Aniline → 3-(3-chloro-phenyl)-5-methyl-2-[1-(9H-purin-6-ylamino)-ethyl]-3H-quinazolin-4-one

HRID 874875

Reaction equation

HRID 874875 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:31])[N:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:6]([CH:12]([NH:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]3[C:17]=1[N:18]=[CH:19][NH:20]3)[CH2:13]C)=[N:7]2.[Cl:32]C1C=C(C=CC=1)N.NC1C=CC=CC=1.O=C1CCC(=O)N1OC(=O)C(NC(OC(C)(C)C)=O)C.O=C1CCC(=O)N1OC(=O)C(NC(OCC1C=CC=CC=1)=O)CC.C(O)(C(F)(F)F)=O.NC1N=C2C(N=CN2)=C(NC(C2N(C3C=CC=C(C)C=3)C(=O)C3C(=CC=CC=3C)N=2)C)N=1>>[Cl:32][C:29]1[CH:30]=[C:25]([N:5]2[C:4](=[O:31])[C:3]3[C:8](=[CH:9][CH:10]=[CH:11][C:2]=3[CH3:1])[N:7]=[C:6]2[CH:12]([NH:15][C:16]2[N:24]=[CH:23][N:22]=[C:21]3[C:17]=2[N:18]=[CH:19][NH:20]3)[CH3:13])[CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 7

HCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 79323-ChloroanilineHCID 100126Succinimido (S)-2-((tert-butoxycarbonyl)amino)propionateHCID 12961228(2,5-Dioxopyrrolidin-1-yl) 2-(phenylmethoxycarbonylamino)butanoateHCID 1784254482-[1-(2-amino-9H-purin-6-ylamino)-ethyl]-3-(3-methylphenyl)-5-methyl-3H-quinazolin-4-oneHCID 178456854HCID 178456854, compound

Product 1

HCID 1784239523-(3-chloro-phenyl)-5-methyl-2-[1-(9H-purin-6-ylamino)-ethyl]-3H-quinazolin-4-one

Procedure

Compound 66 was prepared using the general procedure described above with respect to compound 14, but 3-chloroaniline was substituted for aniline in step A, 2-tert-butoxycarbonylamino-propionic acid 2,5-dioxopyrrolidin-1-yl ester was substituted for 2-benzyloxycarbonylaminobutyric acid 2,5-dioxo-pyrrolidin-1-yl ester in step B, and the alternate procedure (TFA deprotection) was used in step C. 1H NMR (dmso-d6): 8.40-8.31 (m, 2H); 7.73-7.66 (m, 1H); 7.55-7.32 (m, 6H); 5.04-4.86 (m, 1H); 2.72 (s, 3H); 1.52-1.50 (m, 3H). Compound 65 is shown below.

Sources & evidence

ORD record
ord-d2d34b31afff45afab776cc95c4d365a
Source dataset
uspto-grants-2015_03
Patent number
US08980901B2

Linked notes

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