Trifluoroacetic acid → HCID 67242292, compound

HRID 2423162Notes

Reaction equation

HRID 2423162 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]4[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20][O:19][C:15]4=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:31]N1C(=O)CCC1=O.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)(Cl)Cl>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[Cl:31][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[C:15]3[O:19][CH2:20][CH2:21][NH:22][CH2:23][C:14]3=2)[N:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:11]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 31398ChlorosuccinimideHCID 67240578HCID 67240578, compound2×

Product 1

HCID 67242292HCID 67242292, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

tert-Butyl 8-(phenylsulfonyl)-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 17, 15 mg, 0.035 mmol) was dissolved in CHCl3 (2 mL) and N-chlorosuccinimide (7.0 mg, 0.053 mmol) was added. The mixture was heated at 70° C. overnight. The mixture was cooled to room temperature, 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 light yellow solid (4.1 mg) in the form of the trifluoroacetate salt. MS m/z 363 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customevaporated
  3. customThe crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN)

Sources & evidence

ORD record
ord-1f809f5d826546e890284db66446da77
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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