Water → HCID 86629651, compound

HRID 2041301Notes

Reaction equation

HRID 2041301 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[C:7]([C:9]1[CH:25]=[CH:24][C:12]2[CH2:13][CH2:14][N:15](C(=O)C(F)(F)F)[CH2:16][CH2:17][C:11]=2[C:10]=1[S:26][C:27](=[O:31])[N:28]([CH3:30])[CH3:29])#[N:8].O.C(Cl)Cl>CO>[C:9]([O:2][C:1]([N:15]1[CH2:16][CH2:17][C:11]2[C:10]([S:26][C:27](=[O:31])[N:28]([CH3:29])[CH3:30])=[C:9]([C:7]#[N:8])[CH:25]=[CH:24][C:12]=2[CH2:13][CH2:14]1)=[O:4])([CH3:25])([CH3:10])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 86629652HCID 86629652, compound

Product 1

HCID 86629651HCID 86629651, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add potassium carbonate (4.13 g, 30 mmol) to a stirred solution of 7-cyano-6-dimethylcarbamoylsulfanyl-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (740 mg, 2.0 mmol) in methanol (40 mL)/water (15 mL) and stir for 1.5 h. Add DCM (10 mL), di-text-butyl dicarbonate (480 mg, 2.2 mmol) and stir at ambient temperature for 3 days. Concentrate in vacuo and dilute with DCM, wash with water and extract with DCM. Combine the organic layers, wash with brine, dry over MgSO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with EtOAc:heptane (0:1 to 1:1) to give the title compound as a colourless foam (370 mg, 50%). 1H NMR (300 MHz, CDCl3) δ 7.52 (d, J=8 Hz, 1H), 7.29 (d, J=8 Hz, 1H), 3.69-3.48 (m, 4H), 3.26-3.02 (m, 10H), 1.45 (s, 9H).

Workup

  1. concentrationConcentrate in vacuo
  2. additiondilute with DCM
  3. washwash with water
  4. extractionextract with DCM
  5. washwash with brine
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel eluting with EtOAc:heptane (0:1 to 1:1)

Sources & evidence

ORD record
ord-274ae66bc52b4a2f875414586994d911
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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