Water → HCID 66748253, compound

HRID 1622867Notes

Reaction equation

HRID 1622867 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[C:19]3=[N:20][S:21](=[O:25])(=[O:24])[CH2:22][CH2:23][N:18]3[CH2:17][CH2:16][NH:15]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:35])[CH3:34].O>C1COCC1>[C:33]([N:15]1[CH2:16][CH2:17][N:18]2[C:19](=[N:20][S:21](=[O:25])(=[O:24])[CH2:22][CH2:23]2)[C@@H:14]1[C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66747958HCID 66747958, compound

Product 1

HCID 66748253HCID 66748253, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (9S)-9-(4-phenoxyphenyl)-3,4,6,7,8,9-hexahydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide (129 mg), triethylamine (0.100 mL) and acetyl chloride (0.026 mL) in THF (4 mL) was stirred at 0° C. to room temperature for 20 hr. The reaction mixture was added with water, and the precipitate was filtered. The collected solid was purified by recrystallization from MeOH-EtOAc then preparative HPLC (C18, MeCN in H2O with 10 mM NH4HCO3). The combined collected fractions were concentrated in vacuo. The resulting solid was recrystallized from EtOAc-IPE to give the title compound (60 mg) as a white solid.

Workup

  1. filtrationthe precipitate was filtered
  2. customThe collected solid was purified by recrystallization from MeOH-EtOAc
  3. customThe combined collected fractions
  4. concentrationwere concentrated in vacuo
  5. customThe resulting solid was recrystallized from EtOAc-IPE

Sources & evidence

ORD record
ord-47b5d6b029ad492083ccda9573f0d5ef
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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