Triethylamine → {5-[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]-6-fluoropyridin-2-yl}methyl methanesulfonate

HRID 2281043Notes

Reaction equation

[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:18]4[CH:19]=[CH:20][C:21]([CH2:25][OH:26])=[N:22][C:23]=4[F:24])=[C:13]([C:14]([F:17])([F:16])[F:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl.C(OCC)(=O)C>[CH3:34][S:35]([O:26][CH2:25][C:21]1[CH:20]=[CH:19][C:18]([C:12]2[CH:11]=[CH:10][C:9]3[N:5]([CH2:4][CH:1]4[CH2:3][CH2:2]4)[N:6]=[N:7][C:8]=3[C:13]=2[C:14]([F:15])([F:17])[F:16])=[C:23]([F:24])[N:22]=1)(=[O:37])=[O:36]

Participants

Conditions

Temperature: 0 °C

Procedure

{5-[1-(Cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]-6-fluoropyridin-2-yl}methanol (20 mg, 0.055 mmol) was dissolved in dichloromethane (0.36 mL), cooled to 0° C. and treated with triethylamine (0.023 mL, 0.16 mmol) followed by methanesulfonyl chloride (4.7 uL, 0.060 mmol). The mixture was warmed to room temperature and stirred until complete, at which time the mixture was diluted with ethyl acetate and washed with sodium bicarbonate (2×5 mL, aqueous saturated). The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Workup

temperatureThe mixture was warmed to room temperature
washwashed with sodium bicarbonate (2×5 mL, aqueous saturated)
dry with materialThe organic layer was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-a3054d9a800942868776c94784e0857d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139576B2

Reaction notes

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