Acetic Acid → HCID 89649254, compound

HRID 2207600Notes

Reaction equation

CC(C)([O-])C.[K+].C1(S([CH:16]2[CH2:20][C:19]3([CH2:24][CH2:23][N:22]([CH3:25])[C:21]3=[O:26])[NH:18][CH:17]2[C:27]2[CH:32]=[C:31]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=3)[CH:30]=[C:29]([CH3:43])[N:28]=2)(=O)=O)C=CC=CC=1.C(O)(=O)C>C1COCC1>[CH3:25][N:22]1[CH2:23][CH2:24][C:19]2([N:18]=[C:17]([C:27]3[CH:32]=[C:31]([C:33]4[CH:34]=[CH:35][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:38]=4)[CH:30]=[C:29]([CH3:43])[N:28]=3)[CH2:16][CH2:20]2)[C:21]1=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium tert-butoxide (2.22 mL, 3.78 mmol) was added dropwise to a solution of 3-(benzene-sulfonyl)-7-methyl-2-[6-methyl-4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]nonan-6-one (which may be prepared as described in Description 16) (1 g, 1.89 mmol) in THF (20 mL) at 00° C. under N2 and the reaction was stirred at 0° C. for 1 hour. Acetic acid (0.22 mL, 3.78 mmol) was added and the reaction was stirred for 5 minutes. The solid was filtered off and the solvent was evaporated to afford a crude oil. This was purified using a Biotage SP4, 25 g SNAP cartridge, eluting with 0 to 10% MeOH in EtOAc to afford 7-methyl-2-[6-methyl-4-[4-(trifluoromethyl)phenyl]-2-pyridyl]-1,7-diazaspiro[4.4]non-1-en-6-one (641 mg, 1.4892 mmol, 78.9% yield) as a pale yellow oil;

Workup

stirringthe reaction was stirred for 5 minutes
filtrationThe solid was filtered off
customthe solvent was evaporated
customto afford a crude oil
customThis was purified
washeluting with 0 to 10% MeOH in EtOAc

Sources & evidence

ORD record: ord-e6ddd3aa151f4ca1aecdc95a56efa609
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376436B2

Reaction notes

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