17-Hydroxy-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid ethyl ester → 17-[7-Methoxy-8-methyl-2-(6-methyl-pyridin-2-yl)-quinazolin-4-yloxy]-13-methyl-2,14-dioxo-3,13,15-triaza-tricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid

HRID 1443473Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([OH:21])=[N:8][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=3)=[N:10]2)=[CH:5][CH:4]=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>>[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[C:11]2[C:6]([C:7]([O:21][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)=[N:8][C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

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 ester

HCID 178487729HCID 178487729, compound

Product 1

HCID 6842448917-[7-Methoxy-8-methyl-2-(6-methyl-pyridin-2-yl)-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 11.6%

Procedure

Quinazolinol derivative (117) (198 mg, 0.7 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 (50 mg, 10%).

Sources & evidence

ORD record: ord-29a1ca9027634e96907bf1b0f532a79d
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659245B2

Reaction notes

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