Ammonia → HCID 58487884, compound

HRID 1406387Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([O:7][C:8]2[CH:33]=[CH:32][C:11]([CH2:12][NH:13][C:14]([C:16]3([NH:19][C:20]([C:22]4[CH:23]=[N:24][C:25](S(C)(=O)=O)=[N:26][CH:27]=4)=[O:21])[CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)=[C:5]([C:36]([F:39])([F:38])[F:37])[CH:4]=1.[C-:40]#[N:41].[K+].N>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([O:7][C:8]2[CH:33]=[CH:32][C:11]([CH2:12][NH:13][C:14]([C:16]3([NH:19][C:20]([C:22]4[CH:23]=[N:24][C:25]([C:40]#[N:41])=[N:26][CH:27]=4)=[O:21])[CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)=[C:5]([C:36]([F:39])([F:38])[F:37])[CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 50 mg (0.089 mmol) of 2-methanesulphonyl-pyrimidine-5-carboxylic acid{1-[4-(4-methoxy-2-trifluoromethyl-phenoxy)-benzylcarbamoyl]-cyclopropyl}-amide (product from Example 149) in 2 mL DMF was combined with 9 mg (0.13 mmol) of potassium cyanide and then heated to 100° C. for 10 minutes in a microwave apparatus. The mixture was then combined with 2 mL concentrated ammonia solution and extracted with dichloromethane. The crude product obtained after evaporation was purified by chromatography (reversed phase HPLC).

Workup

extractionextracted with dichloromethane

Sources & evidence

ORD record: ord-43e41f62ff844a8883b0967643cbac3d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916589B2

Reaction notes

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