Triethylamine → HCID 73041485, compound

HRID 734813Notes

Reaction equation

Cl.[CH3:2][O:3][NH2:4].C(N(CC)CC)C.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[C:26][C:27]3[CH:28]=[CH:29][C:30]([O:35][CH2:36][CH2:37][N:38]4[CH2:43][CH2:42][CH:41]([CH3:44])[CH2:40][CH2:39]4)=[C:31]([CH:34]=3)[CH:32]=O)=[N:23][CH:24]=2)=[CH:15][CH:14]=1>C(#N)C.CCO.O>[CH3:2][O:3][N:4]=[CH:32][C:31]1[CH:34]=[C:27]([C:26]#[C:25][C:22]2[CH:21]=[CH:20][C:19]([C:16]3[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=3)=[CH:24][N:23]=2)[CH:28]=[CH:29][C:30]=1[O:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][CH:41]([CH3:44])[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 75 °C

Procedure

22 mg (0.257 mmol) of O-methylhydroxylamine hydrochloride and 36 μL (0.257 mmol) of triethylamine were added to a solution of 85 mg (0.185 mmol) of 5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-[2-(4-methylpiperidin-1-yl)ethoxy]benzaldehyde (Example 14.1c) in 2 mL of acetonitrile/EtOH (1:1) and the mixture was stirred for 16 hours at 75° C. The reaction mixture was diluted with water and the aqueous phase exhaustively extracted with DCM. The combined organic phases were dried over magnesium sulfate and evaporated down in vacuo. Yield: 40 mg (44% of theoretical); C29H30ClNO3O2 (M=488.020); calc.: molpeak (M+H)+: 488/490 (Cl); found: molpeak (M+H)+: 488/490 (Cl); HPLC-MS: 6.04 minutes (method A).

Workup

extractionthe aqueous phase exhaustively extracted with DCM
dry with materialThe combined organic phases were dried over magnesium sulfate
customevaporated down in vacuo
custom6.04 minutes (method A)

Sources & evidence

ORD record: ord-84265fcc88ff4db0afc25fb5cea8a7bb
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592358B2

Reaction notes

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