HCID 67060301, compound → HCID 67060327, compound

HRID 1625113Notes

Reaction equation

HRID 1625113 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[N:11]1[C:19](=[O:20])[CH:14]2[CH2:15][S:16][CH2:17][CH2:18][N:13]2[C:12]1=[O:21]>CO>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([N:11]2[C:19](=[O:20])[CH:14]3[CH2:15][S:16][CH2:17][CH2:18][N:13]3[C:12]2=[O:21])=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 1

HCID 67060301HCID 67060301, compound

Product 1

HCID 67060327HCID 67060327, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 2-(2-chloro-4-nitrophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dione (124 mg, 0.38 mmol) and 5% Pt sulfided on carbon (148 mg, 0.04 mmol) were added to a flask under argon. Methanol (8 mL) was added. The flask was purged with vacuum and H2 gas, then H2 gas was applied by balloon (1 atm) with stirring for about 18 hours. The mixture was diluted with MeOH and poured through Celite, washing with MeOH. The filtrate was concentrated under vacuum to give about 125 mg of crude product. The compound was purified by chromatography on silica gel (12 g) eluting with a 0-to-50% A-to-B gradient (A is DCM: B is 10% MeOH/DCM with 1% ammonium hydroxide) to give 67 mg of 2-(4-amino-2-chlorophenyl)tetrahydro-1H-imidazo[5,1-c][1,4]thiazine-1,3(2H)-dione, 1.2.40.

Workup

  1. additionwere added to a flask under argon
  2. customThe flask was purged with vacuum and H2 gas
  3. additionThe mixture was diluted with MeOH
  4. additionpoured through Celite
  5. washwashing with MeOH
  6. concentrationThe filtrate was concentrated under vacuum
  7. customto give about 125 mg of crude product
  8. customThe compound was purified by chromatography on silica gel (12 g)
  9. washeluting with a 0-to-50% A-to-B gradient (A is DCM

Sources & evidence

ORD record
ord-583cae61dba44ac19762adf520f7c391
Source dataset
uspto-grants-2014_07
Patent number
US08779157B2

Reaction notes

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