2-Amino-6-chlorobenzoic acid → 2-[2-tert-butoxy-1-(9H-purin-6-ylamino)-ethyl]-3-phenyl-3H-quinazolin-4-one

HRID 221310

Reaction equation

HRID 221310 reaction equation
C[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)CC)=[N:7]2.NC1C=CC=C(Cl)C=1C(O)=O.NC1C=CC=C(C)C=1C(O)=O.O=C1CCC(=O)N1OC(=O)C(NC(OCC1C=CC=CC=1)=O)[CH2:64][O:65][C:66]([CH3:69])([CH3:68])[CH3:67].O=C1CCC(=O)N1OC(=O)C(NC(OCC1C=CC=CC=1)=O)CC>>[C:66]([O:65][CH2:64][CH:12]([C:6]1[N:5]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:4](=[O:31])[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][CH:2]=2)[N:7]=1)[NH:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][NH:20]2)([CH3:69])([CH3:68])[CH3:67]

Participants

6

Reactant 5

HCID 750712-Amino-6-chlorobenzoic acidHCID 1512106-Methylanthranilic acidHCID 2729196Z-O-tert-butyl-L-serine N-hydroxysuccinimide esterHCID 12961228(2,5-Dioxopyrrolidin-1-yl) 2-(phenylmethoxycarbonylamino)butanoateHCID 178456854HCID 178456854, compound

Product 1

HCID 1784505052-[2-tert-butoxy-1-(9H-purin-6-ylamino)-ethyl]-3-phenyl-3H-quinazolin-4-one

Procedure

2-[2-tert-butoxy-1-(9H-purin-6-ylamino)-ethyl]-3-phenyl-3H-quinazolin-4-one was prepared using the general procedure described above with respect to compound 14, but 2-amino-6-chlorobenzoic acid was substituted for 2-amino-6-methylbenzoic acid in step A, 2-benzyloxycarbonylamino-3-tert-butoxy-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester was substituted for 2-benzyloxycarbonylaminobutyric acid 2,5-dioxo-pyrrolidin-1-yl ester in step B, and the conditions used in step C removed both the benzyl protecting group and the A-Ring chloro substituent.

Workup

  1. customremoved both the benzyl protecting group

Sources & evidence

ORD record
ord-323a7b7e7bd74b7289b501d3ed21f73b
Source dataset
uspto-grants-2012_06
Patent number
US08207153B2

Linked notes

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