1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → 6-Amino-4-[3-chloro-4-(2-pyridylmethoxy)anilino]quinazoline

HRID 1675229Notes

Reaction equation

HRID 1675229 reaction equation
C(OC(=O)NCC(=O)[NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][N:15]=[C:14]2[NH:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34]C=C(F)C=2)=[C:24]([Cl:37])[CH:23]=1)(C)(C)C.C(OC([N:47]1CC[CH2:49][C@H:48]1C(O)=O)=O)(C)(C)C>>[Cl:37][C:24]1[CH:23]=[C:22]([NH:21][C:14]2[C:13]3[C:18](=[CH:19][CH:20]=[C:11]([NH2:10])[CH:12]=3)[N:17]=[CH:16][N:15]=2)[CH:27]=[CH:26][C:25]=1[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:49]=[CH:48][N:47]=1

Participants

3

Reactant 2

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 11570293({4-[3-Chloro-4-(3-fluoro-benzyloxy)-phenylamino]-quinazolin-6-ylcarbamoyl}-methyl)-carbamic acid t-butylester

Product 1

HCID 189676876-Amino-4-[3-chloro-4-(2-pyridylmethoxy)anilino]quinazoline

Procedure

The procedure of (1-5) of Example 1 was repeated except for using 414 mg of (2S)-pyrrolidine-1,2-dicarboxylic acid-1-t-butylester instead of 2-t-butoxycarbonylamino-ethanoic acid and 368 mg of the compound obtained in (145-2) to obtain the title compound (200 mg, 35%).

Sources & evidence

ORD record
ord-7c521ce2b07d4ad3841086e94ee29950
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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