Triethylamine → HCID 86683492, compound

HRID 515838Notes

Reaction equation

[C:1]([C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:16](=[O:17])[C:12]3([CH2:15][CH2:14][CH2:13]3)[N:11]([C:18]3[CH:30]=[CH:29][C:21]([C:22]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])=[O:23])=[C:20]([F:31])[CH:19]=3)[C:10]2=[S:32])=[CH:5][C:4]=1[C:33]([F:36])([F:35])[F:34])#[N:2].C(N(CC)CC)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46].CCOC(C)=O>C1COCC1.[Cl-].[Na+].O>[CH3:44][S:45]([O:28][CH2:27][CH2:26][CH2:25][NH:24][C:22](=[O:23])[C:21]1[CH:29]=[CH:30][C:18]([N:11]2[C:10](=[S:32])[N:9]([C:6]3[CH:7]=[N:8][C:3]([C:1]#[N:2])=[C:4]([C:33]([F:35])([F:34])[F:36])[CH:5]=3)[C:16](=[O:17])[C:12]32[CH2:13][CH2:14][CH2:15]3)=[CH:19][C:20]=1[F:31])(=[O:47])=[O:46]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluoro-N-(3-hydroxypropyl)benzamide (Compound 306, 80 mg, 0.15 mmol) and triethylamine (22 μL, 0.16 mmol) in THF (5 mL) was cooled to 0° C. Methanesulfonyl chloride (23 μL, 0.3 mmol) was added dropwise and the mixture was stirred at room temperature overnight. Brine and EtOAc were added and the aqueous layer was extracted with EtOAc (2×), the organics were combined, dried over sodium sulfate, and evaporated to dryness to afford crude 3-(4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluorobenzamido)propyl methanesulfonate that was used as is.

Workup

extractionthe aqueous layer was extracted with EtOAc (2×)
dry with materialdried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-f0964d6256c549c0b2f39b52617c0b47
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108944B2

Reaction notes

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