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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-(7-Methoxy-6-methyl-2-phenyl-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

HRID 1443475
Notes
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Reaction equation

HRID 1443475 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([OH:19])=[N:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10]2)=[CH:5][C:4]=1[CH3:20].C([O:23][C:24]([C:26]12[CH2:43][CH:42]1[CH:41]=[CH:40][CH2:39][CH2:38][CH2:37][CH2:36][N:35]([CH3:44])[C:34](=[O:45])[N:33]1[CH:29]([CH2:30][CH:31](O)[CH2:32]1)[C:28](=[O:47])[NH:27]2)=[O:25])C>>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:19][CH:31]3[CH2:30][CH:29]4[N:33]([C:34](=[O:45])[N:35]([CH3:44])[CH2:36][CH2:37][CH2:38][CH2:39][CH:40]=[CH:41][CH:42]5[C:26]([C:24]([OH:25])=[O:23])([NH:27][C:28]4=[O:47])[CH2:43]5)[CH2:32]3)=[N:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:10]2)=[CH:5][C:4]=1[CH3:20]
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 6841037217-Hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid ethyl esterHCID 178486781HCID 178486781, compound

Product 1

HCID 6840939017-(7-Methoxy-6-methyl-2-phenyl-quinazolin-4-yloxy)-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acidYield 11.3%

Procedure

Quinazolinol derivative 112 (200 mg, 0.53 mmol) was coupled to compound 51 (268 mg, 0.7 mmol) followed by hydrolysis of the ethyl ester as described in example 52 which gave the title compound (36 mg, 11%). MS (M−H)+ 600.

Sources & evidence

ORD record
ord-94e988e5c6984b529aa4c003ec2dee9e
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07659245B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes