Methanesulfonyl chloride → HCID 86695212, compound

HRID 1504055Notes

Reaction equation

[CH2:1]1[C:4]2([CH2:7][N:6]([CH:8]3[CH2:13][CH2:12][CH:11]([O:14][C:15]4[N:16]=[CH:17][N:18]=[C:19]5[C:26]=4[C:25]4[C@@H:24]([CH2:27][OH:28])[CH2:23][CH2:22][C:21]=4[S:20]5)[CH2:10][CH2:9]3)[CH2:5]2)[CH2:3][O:2]1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH3:29][S:30]([O:28][CH2:27][C@H:24]1[CH2:23][CH2:22][C:21]2[S:20][C:19]3[C:26](=[C:15]([O:14][CH:11]4[CH2:12][CH2:13][CH:8]([N:6]5[CH2:7][C:4]6([CH2:3][O:2][CH2:1]6)[CH2:5]5)[CH2:9][CH2:10]4)[N:16]=[CH:17][N:18]=3)[C:25]1=2)(=[O:32])=[O:31]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of [(3S)-12-[(4-[2-oxa-6-azaspiro[3.3]heptan-6-yl]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]methanol (250 mg, 0.62 mmol, 1.00 equiv) and TEA (188 mg, 1.86 mmol, 2.99 equiv) in dichloromethane (10 mL) was added MsCl (142 mg, 1.25 mmol, 2.00 equiv) and the resulting mixture was stirred for 1 h at 25° C. under nitrogen. After completion, the reaction was quenched with water and extracted with 3×50 mL of ethyl acetate. The organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The solvents were concentrated under reduced pressure vacuum to afford [(3S)-12-[(4-[2-oxa-6-azaspiro[3.3]heptan-6-yl]cyclohexyl)oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-3-yl]methyl methanesulfonate (250 mg, crude) as a yellow oil.

Workup

customAfter completion, the reaction was quenched with water
extractionextracted with 3×50 mL of ethyl acetate
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationThe solvents were concentrated under reduced pressure vacuum

Sources & evidence

ORD record: ord-c4d07f87d1cb402cba0ce5620632d97f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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