Potassium tert-butoxide → USRE47493, Example 4

HRID 517232Notes

Reaction equation

HRID 517232 reaction equation
CC(C)([O-])C.[K+].[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:30]2[C:40](=[O:41])[CH2:39][C:33]3([CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH2:32][C:31]=2OC)[NH:16][C:17]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)=[O:18])=[CH:11][CH:10]=1)#[N:8]>CN(C)C=O>[O:18]=[C:17]1[NH:16][CH:15]([C:12]2[CH:13]=[CH:14][C:9]([C:7]#[N:8])=[CH:10][CH:11]=2)[C:30]2[C:40](=[O:41])[CH2:39][C:33]3([CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)[CH2:32][C:31]=2[N:19]1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 867323001-((4-Cyanophenyl)(8-methoxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl)urea2×

Product 1

HCID 86732353USRE47493, Example 4

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (49 mg, 0.44 mmol) is added to a solution of 1-((4-cyanophenyl)-(8-methoxy-10-oxo-3-oxaspiro[5.5]undec-8-en-9-yl)methyl)-3-(3-(trifluoromethyl)phenyl) urea (intermediate 11, 224 mg, 0.44 mmol) in N,N-dimethylformamide (3 mL). The mixture is stirred at room temperature over night and then purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 21 mg; ESI mass spectrum [M+H]+=482, Retention time HPLC: 1.04 min (V011_S01).

Workup

  1. custompurified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  2. custom1.04 min (V011_S01)

Sources & evidence

ORD record
ord-12815db6c6584c679867f10beedd4619
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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