4-Methylmorpholine → {2-Amino-6-[2-(4-methylpiperazine-1-carbonyl)phenyl]quinazolin-4-yl}-(1,3-dihydroisoindol-2-yl)methanone

HRID 1037682Notes

Reaction equation

F[B-](F)(F)F.[N:6]1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.N1CCCC1.[CH3:28][N:29]1[CH2:34][CH2:33]O[CH2:31][CH2:30]1.[NH2:35][C:36]1[N:45]=[C:44]([C:46]([N:48]2[CH2:56][C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH2:49]2)=[O:47])[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([C:57]3[CH:65]=[CH:64][CH:63]=[CH:62][C:58]=3[C:59]([OH:61])=O)[CH:42]=2)[N:37]=1>CN(C)C=O>[NH2:35][C:36]1[N:45]=[C:44]([C:46]([N:48]2[CH2:56][C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH2:49]2)=[O:47])[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([C:57]3[CH:65]=[CH:64][CH:63]=[CH:62][C:58]=3[C:59]([N:6]3[CH2:31][CH2:30][N:29]([CH3:28])[CH2:34][CH2:33]3)=[O:61])[CH:42]=2)[N:37]=1

Participants

Conditions

Temperature: 25 °C

Procedure

175.9 mg of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), 33.8 μl of pyrrolidine and 200.9 μl of 4-methylmorpholine are added to a solution of 150 mg of 2-[2-amino-4-(1,3-dihydroisoindole-2-carbonyl)quinazolin-6-yl]benzoic acid in 1 ml of dimethylformamide. The mixture is subsequently stirred at 25° C. for 12 h. The mixture is evaporated to dryness in vacuo, the residue is taken up in 1 ml of dimethyl sulfoxide and purified by chromatography (reversed phase HPLC).

Workup

customThe mixture is evaporated to dryness in vacuo
custompurified by chromatography (reversed phase HPLC)

Sources & evidence

ORD record: ord-f54c5ad49e014392a4085eabc77f567e
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546565B2

Reaction notes

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