Water → HCID 66748253, compound

HRID 1748132Notes

Reaction equation

HRID 1748132 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-382bacd362a3421f8565ad44aaf7151c
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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