Thiophenol → HCID 56651603, compound

HRID 2369816Notes

Reaction equation

HRID 2369816 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:24][C:25]2[C:34]3[C:29](=[C:30]([C:35]([NH2:37])=[O:36])[CH:31]=[CH:32][CH:33]=3)[N:28]=[C:27]([CH3:38])[N:26]=2)[CH2:9][N:10]([CH3:23])S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(S)C=CC=CC=1>CC#N>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:24][C:25]2[C:34]3[C:29](=[C:30]([C:35]([NH2:37])=[O:36])[CH:31]=[CH:32][CH:33]=3)[N:28]=[C:27]([CH3:38])[N:26]=2)[CH2:9][NH:10][CH3:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 66714522HCID 66714522, compound

Product 1

HCID 56651603HCID 56651603, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Crude 4-[((1S)-1-(4-Fluorophenyl)-2-{methyl[(4-nitrophenyl)sulfonyl]amino}ethyl)-amino]-2-methylquinazoline-8-carboxamide (161 mg; 0.30 mmol) and Cs2CO3 (488 mg; 1.50 mmol) were suspended in CH3CN (7 ml), and stirred for 10 minutes at room temperature. Benzenethiol (0.12 ml; 1.20 mmol) was added via syringe and the solution was stirred vigorously at room temperature overnight. The reaction mixture was concentrated, dissolved in DMSO (3 ml), and purified via Reverse Phase chromatography (Yamazen, basic buffer) to provide 9 16? (46 mg; 43% yield) as the free base. LC-MS [354 (M+1)]

Workup

  1. stirringthe solution was stirred vigorously at room temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in DMSO (3 ml)
  4. custompurified via Reverse Phase chromatography (Yamazen, basic buffer)
  5. customto provide 9 16

Sources & evidence

ORD record
ord-d2903218fb8349ee8e15bb9c668d7ade
Source dataset
uspto-grants-2014_04
Patent number
US08710044B2

Reaction notes

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