Trifluoroacetic acid → HCID 67242915, compound

HRID 2423165Notes

Reaction equation

HRID 2423165 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[O:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][C:9]3=2)[NH:4][CH:3]=1.[H-].[Na+].[C:25]([C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1)#[N:26].[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>CN(C=O)C>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[O:15][CH2:14][CH2:13][NH:12][CH2:11][C:9]3=2)[N:4]([S:33]([C:29]2[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=2)[C:25]#[N:26])(=[O:35])=[O:34])[CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24758Sodium hydrideHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 69036330HCID 69036330, compound2×

Product 1

HCID 67242915HCID 67242915, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

tert-Butyl 10-chloro-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 20, 10 mg, 0.031 mmol) was dissolved in DMF (1 mL) and sodium hydride (60% in mineral oil, 2.5 mg, 0.062 mmol) was added. The mixture was stirred for 10 minutes at room temperature before 3-cyanobenzene-1-sulfonyl chloride (13 mg, 0.062 mmol) was added. The reaction mixture was stirred for 20 minutes before TFA (2 mL) was added and the mixture was heated at 50° C. overnight. The reaction mixture was evaporated and the crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN) to give the title compound as an off-white solid (1.3 mg) in the form of the trifluoroacetate salt. MS m/z 388 [M+H]+.

Workup

  1. additionwas added
  2. additionwas added
  3. customThe reaction mixture was evaporated
  4. customthe crude material was purified by preparative HPLC (ACE C8, 0.1% TFA-CH3CN)

Sources & evidence

ORD record
ord-99f6e0b629604157842ed095d63b8d7f
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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