Methanol → HCID 46829881, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][C:19]#N)[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:21]([CH3:23])[CH3:22])=[CH:4][CH:3]=1.[OH-:24].[K+].C[OH:27]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]([CH2:18][C:19]([OH:27])=[O:24])[CH2:15][CH2:16][CH2:17][C:12]=3[N:11]=[C:10]2[CH:21]([CH3:23])[CH3:22])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 160 °C
Procedure
A solution of Intermediate 42 (45 mg) in methanol (0.4 ml) was treated with 4.5M potassium hydroxide (0.2 ml). The reaction vessel was sealed and heated in CEM Discover using initial 50 W to 150° C. for 30 mins. The mixture was reheated in the microwave at 150° C. for 1 h. A further aliquot of 4.5M potassium hydroxide (0.05 ml) was added and the mixture was heated in the microwave at 160° C. for 30 mins. A further aliquot of 4.5M potassium hydroxide (0.05 ml) was added and the mixture was heated in the microwave at 160° C. for 1 h. The mixture was filtered through a frit and the filtrate diluted with DMSO to 1 ml. The sample was purified by MDAP (Method A). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the product (39.2 mg)
Workup
- customThe reaction vessel was sealed
- temperatureheated in CEM Discover
- customfor 30 mins
- temperaturethe mixture was heated in the microwave at 160° C. for 1 h
- filtrationThe mixture was filtered through a frit
- additionthe filtrate diluted with DMSO to 1 ml
- customThe sample was purified by MDAP (Method A)
- customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
Sources & evidence
- ORD record
- ord-4331c92014394e45abf75b8658889c61
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399444B2
Reaction notes
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