Dimethyl Sulfide → HCID 58551405, compound

HRID 2204262Notes

Reaction equation

HRID 2204262 reaction equation
ClN1C(=O)CCC1=O.[CH3:9][S:10][CH3:11].[CH:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([N:24]2[CH2:41][CH2:40][C:27]3([C:32]4=[CH:33][CH:34]=C[N:31]4[C:30]4[CH:36]=[CH:37][CH:38]=[CH:39][C:29]=4[O:28]3)[CH2:26][CH2:25]2)=[O:23])=[CH:18][C:17]=1[CH3:42])([CH3:14])[CH3:13]>ClCCl.C1(C)C=CC=CC=1>[CH:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([N:24]2[CH2:41][CH2:40][C:27]3([O:28][C:29]4[CH:39]=[CH:38][CH:37]=[CH:36][C:30]=4[N:31]4[C:9]([S:10][CH3:11])=[CH:34][CH:33]=[C:32]34)[CH2:26][CH2:25]2)=[O:23])=[CH:18][C:17]=1[CH3:42])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 58551586HCID 58551586, compound

Product 1

HCID 58551405HCID 58551405, compoundYield 110.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1-chloropyrrolidine-2,5-dione (92 mg, 0.70 mmol) in dry dichloromethane (3.2 mL) was added dropwise at −10° C. to a solution of methylsulfanylmethane (82 μL, 1.1 mmol) in dry dichloromethane (800 μL) over a period of 5 minutes. The reaction was allowed to warm to room temperature and was stirred for 30 minutes. The mixture was then cooled to −55° C. and a solution of (4-isopropoxy-3-methyl-phenyl)-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-yl-methanone (210 mg, 0.49 mmol) in dry dichloromethane (800 μL) was added dropwise. The cooling bath was removed and the mixture was gradually warmed up to room temperature and was stirred overnight. The solvent was removed under vacuum and the pink residue that was obtained was dissolved in dry toluene (7 mL) and was heated at 50° C. for 5 minutes. The solvent was removed to afford (4-isopropoxy-3-methylphenyl)(1-(methylthio)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)methanone (250 mg, 78%). ESI-MS m/z calc. 462.2, found 463.5 (M+1)+; Retention time: 2.43 minutes (3 min run).

Workup

  1. temperatureThe mixture was then cooled to −55° C.
  2. customThe cooling bath was removed
  3. temperaturethe mixture was gradually warmed up to room temperature
  4. stirringwas stirred overnight
  5. customThe solvent was removed under vacuum
  6. customthe pink residue that was obtained
  7. temperaturewas heated at 50° C. for 5 minutes
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-c3e329223ec24029af9c62d53ad5a7de
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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