Trifluoroacetic acid → HCID 67240942, compound

HRID 2423168Notes

Reaction equation

HRID 2423168 reaction equation
[CH2:1]1[C:7]2=[C:8]3[C:12](=[CH:13][CH:14]=[C:6]2[O:5][CH2:4][CH2:3][N:2]1C(OC(C)(C)C)=O)[NH:11][CH:10]=[CH:9]3.[H-].[Na+].[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31](Cl)(=[O:33])=[O:32].[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>CN(C=O)C>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([N:11]1[C:12]2[C:8](=[C:7]3[CH2:1][NH:2][CH2:3][CH2:4][O:5][C:6]3=[CH:14][CH:13]=2)[CH:9]=[CH:10]1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24758Sodium hydrideHCID 761872-Chlorobenzenesulfonyl chlorideHCID 67242130HCID 67242130, compound2×

Product 1

HCID 67240942HCID 67240942, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DMF (1 mL) was added to a mixture of tert-butyl 1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 18, 10.0 mg, 0.035 mmol) and 60% NaH (5.56 mg, 0.139 mmol). The reaction mixture was stirred for 10 minutes at room temperature before 2-chlorophenylsulfonyl chloride (11 mg, 0.052 mmol) was added all in one portion. After 30 minutes TFA (1 mL) was added and the mixture was stirred for 10 minutes and evaporated. The crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN) to give the title compound as a white solid (9.6 mg) in the form of the trifluoroacetate salt. MS m/z 363 [M+H]+.

Workup

  1. additionwas added all in one portion
  2. customevaporated
  3. customThe crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN)

Sources & evidence

ORD record
ord-7a8356bc4bcc4c38b4e07e3094ee0eb0
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

Loading…