Water → HCID 86670902, compound

HRID 1521840Notes

Reaction equation

HRID 1521840 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[S:10](=[O:12])(=[O:11])[CH2:9][C:8]3[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:14][N:15]([CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[C:7]=3[C:5]=2[N:6]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:36])[CH3:35].O>C(Cl)Cl>[C:34]([NH:1][C:2]1[S:3][C:4]2[S:10](=[O:12])(=[O:11])[CH2:9][C:8]3[C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:14][N:15]([CH:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[C:7]=3[C:5]=2[N:6]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86670900HCID 86670900, compound

Product 1

HCID 86670902HCID 86670902, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To suspension of ethyl 7-amino-1-(tetrahydro-2H-pyran-4-yl)-1,4-dihydropyrazolo[3′,4′:4,5]thiopyrano[3,2-d][1,3]thiazole-3-carboxylate 5,5-dioxide (71 mg; 0.18 mmol; 1 eq.) and triethylamine (98.8 μL; 0.71 mmol; 4 eq.) in DCM (710 μL) at 0° C. is added acetylchloride (30 μL; 0.46 mmol; 2.5 eq.). The suspension is stirred at rt overnight then heated up to 100° C. for 1 day. Water is added to reacture mixture and the product is extracted with DCM (×2). The combined organic layers are washed with brine, dried over Na2SO4 then concentrated under vacuum affording a beige solid residue. The residue is triturated then sonicated in Et2O and the solid is filtered-off to afford the title compound. HPLC (max plot) 98.8%; Rt 3.28 min. MS (ESI+): 441.1.

Workup

  1. temperaturethen heated up to 100° C. for 1 day
  2. extractionthe product is extracted with DCM (×2)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationthen concentrated under vacuum
  6. customaffording a beige solid residue
  7. customThe residue is triturated
  8. customthen sonicated in Et2O

Sources & evidence

ORD record
ord-997fdba36bc043ce963e15a422b86494
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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