Chloride → HCID 18613468, compound

HRID 1265790Notes

Reaction equation

HRID 1265790 reaction equation
[Cl:1][C:2]1[C:3]([N:27]([CH3:29])[CH3:28])=[CH:4][C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N:18]4[C:22](O)=[C:21](C)[N:20]=[N:19]4)[CH:13]=3)[CH2:9][C:8](=[O:25])[NH:7][C:6]=2[CH:26]=1.O=S(Cl)Cl.[Na+].[I-].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.[Cl-].[CH2:42](Cl)Cl>CCOC(C)=O>[Cl:1][C:2]1[C:3]([N:27]([CH3:28])[CH3:29])=[CH:4][C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N:18]4[C:22]([CH2:42][N:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)=[CH:21][N:20]=[N:19]4)[CH:13]=3)[CH2:9][C:8](=[O:25])[NH:7][C:6]=2[CH:26]=1

Participants

8

Reactant 6

HCID 312ChlorideHCID 5238Sodium IodideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 178434694HCID 178434694, compound

Product 1

HCID 18613468HCID 18613468, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from 8-chloro-7-dimethylamino-4-[3-(5-hydroxy-methyl-[1,2,3]triazol-1-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 3) (123 mg, 0.3 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 (0.248 mL, 3.0 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 (101 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-f323df2f447c40e9924e0afc3f0308cf
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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