Aminoacetaldehyde dimethyl acetal → HCID 178495894, compound

HRID 388541Notes

Reaction equation

[NH2:1][C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:8]([CH3:19])[CH2:7]2)[N:5]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][CH:28]=2)[C:4](=[O:37])[N:3]=1.[CH3:38][O:39][CH:40]([O:43][CH3:44])[CH2:41]N>CCOC(C)=O>[CH2:12]([N:9]1[CH2:10][CH2:11][C:6]2([N:5]([C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=3[C:27]3[CH:28]=[CH:29][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:31][CH:32]=3)[C:4](=[O:37])[N:3]=[C:2]2[NH:1][CH2:41][CH:40]([O:43][CH3:44])[O:39][CH3:38])[CH2:7][CH:8]1[CH3:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of 4-amino-8-benzyl-1-[4-fluoro-4′-(methylsulfonyl)biphenyl-2-yl]-7-methyl-1,3,8-triazaspiro[4.5]dec-3-en-2-one (50 mg, 0.10 mmol) in 2,2-dimethoxyethylamine (2.0 ml) was sealed and allowed to stir at 85° C. for 18 h. The temperature was increased to 110° C., and the reaction was allowed to stir for an additional 16 h. The reaction was diluted with EtOAc and washed with brine. The organic portion was dried over sodium sulfate, filtered, and concentrated in vacuo to yield 8-benzyl-4-[(2,2-dimethoxyethyl)amino]-1-[4-fluoro-4′-(methylsulfonyl)biphenyl-2-yl]-7-methyl-1,3,8-triazaspiro[4.5]dec-3-en-2-one. LCMS (M+H) 609.0.

Workup

temperatureThe temperature was increased to 110° C.
stirringto stir for an additional 16 h
washwashed with brine
dry with materialThe organic portion was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-341fa07134824e02b377d02a53ec4546
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377954B2

Reaction notes

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