Chloride → HCID 18548754, compound

HRID 1266866Notes

Reaction equation

HRID 1266866 reaction equation
O[CH2:2][C:3]1[N:7]([C:8]2[CH:9]=[C:10]([C:14]3[CH2:20][C:19](=[O:21])[NH:18][C:17]4[CH:22]=[C:23]([C:28]([F:31])([F:30])[F:29])[C:24]([O:26][CH3:27])=[CH:25][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[N:6]=[N:5][CH:4]=1.O=S(Cl)Cl.[Na+].[I-].[NH:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1.[Cl-]>C(Cl)Cl.CCOC(C)=O>[CH3:27][O:26][C:24]1[C:23]([C:28]([F:30])([F:31])[F:29])=[CH:22][C:17]2[NH:18][C:19](=[O:21])[CH2:20][C:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([N:7]4[C:3]([CH2:2][N:38]5[CH2:42][CH2:41][CH2:40][CH2:39]5)=[CH:4][N:5]=[N:6]4)[CH:9]=3)=[N:15][C:16]=2[CH:25]=1

Participants

8

Reactant 5

HCID 312ChlorideHCID 5238Sodium IodideHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 18548922HCID 18548922, compound

Product 1

HCID 18548754HCID 18548754, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 4-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-7-methoxy-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 46) (86 mg, 0.2 mmol) by treatment with SOCl2 (0.044 mL, 0.6 mmol) in CH2Cl2 (2 mL) from 23° C. to reflux for 15 min, followed by evaporation to dryness. The crude chloride was dissolved in DMF (2 mL) and stirred with cat. amount of NaI and pyrrolidine (0.17 mL, 2.0 mmol) at 23° C. until tlc indicated complete conversion of the chloride. The reaction mixture was taken up in EtOAc, washed with water and brine, dried over Na2SO4. Removal of the solvent in vacuum left a yellow semisolid, which was purified by silica gel column chromatography. Obtained as a yellow solid (47 mg).

Workup

  1. temperatureto reflux for 15 min
  2. customfollowed by evaporation to dryness
  3. dissolutionThe crude chloride was dissolved in DMF (2 mL)
  4. customat 23° C.
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. customRemoval of the solvent in vacuum
  8. waitleft a yellow semisolid, which
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3cd541603b1944debad1083886a8b05c
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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