17-Hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid ethyl ester → 17-[2-(4-Fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([OH:18])[C:15]3[C:10](=[C:11]([CH3:21])[C:12]([O:19][CH3:20])=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.C([O:24][C:25]([C:27]12[CH2:44][CH:43]1[CH:42]=[CH:41][CH2:40][CH2:39][CH2:38][CH2:37][N:36]([CH3:45])[C:35](=[O:46])[N:34]1[CH:30]([CH2:31][CH:32](O)[CH2:33]1)[C:29](=[O:48])[NH:28]2)=[O:26])C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:17]=[C:16]([O:18][CH:32]3[CH2:31][CH:30]4[N:34]([C:35](=[O:46])[N:36]([CH3:45])[CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH:42][CH:43]5[C:27]([C:25]([OH:26])=[O:24])([NH:28][C:29]4=[O:48])[CH2:44]5)[CH2:33]3)[C:15]3[C:10](=[C:11]([CH3:21])[C:12]([O:19][CH3:20])=[CH:13][CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1Participants
3
Reactant 2
Product 1
Procedure
Quinazolinol derivative (92) (141 mg, 0.5 mmol) was coupled to compound 51 (170 mg, 0.45 mmol) as described in example 52, which gave the crude ethyl ester of the title compound. The crude ester was purified by flash chromatography on silica gel eluted with 5→15% MeOH in diethyl ether, the afforded residue was dissolved in dichloromethane and filtered to remove traces of silica, which gave the ethyl ester of the title compound (135 mg, 46%). The ethyl ester was then hydrolyzed as described in example 52, which gave the title compound (125 mg, 100%)
Sources & evidence
- ORD record
- ord-6053d68f4f274d6488f10a2958701a08
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07659245B2
Reaction notes
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