Water → 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenyl trifluoromethanesulfonate

HRID 1748097Notes

Reaction equation

HRID 1748097 reaction equation
[O:1]=[S:2]1(=[O:19])[CH2:7][CH2:6][N:5]2[CH2:8][CH2:9][CH2:10][C@@H:11]([C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)[C:4]2=[N:3]1.C(=O)([O-])[O-].[K+].[K+].[F:26][C:27]([F:33])([F:32])[S:28](Cl)(=[O:30])=[O:29].O>CN(C=O)C>[F:26][C:27]([F:33])([F:32])[S:28]([O:18][C:15]1[CH:16]=[CH:17][C:12]([C@H:11]2[C:4]3=[N:3][S:2](=[O:1])(=[O:19])[CH2:7][CH2:6][N:5]3[CH2:8][CH2:9][CH2:10]2)=[CH:13][CH:14]=1)(=[O:30])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79000Trifluoromethanesulfonyl chlorideHCID 667484964-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol

Product 1

HCID 866636154-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (1.00 g) and potassium carbonate (1.23 g) in DMF (dry) (30 mL) was added trifluoromethanesulfonyl chloride (0.939 mL) at 0° C. The mixture was stirred at 0° C. for 5 min then at room temperature for 2 hr. The mixture was added with water. The resulting precipitate was collected, washed with water, and dried at 60° C. in vacuo to give the title compound (1.27 g) as a white solid.

Workup

  1. waitat room temperature for 2 hr
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-d8071c7a09bb4cc496913457e5fd724e
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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