Triphenylphosphine → HCID 67448485, compound

HRID 1853706Notes

Reaction equation

HRID 1853706 reaction equation
O[CH2:2][CH:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]3[C:17]4[CH:30]=[CH:29][S:28][C:18]=4[C:19](=[O:27])[NH:20][C:21]=3[CH:22]=[CH:23][C:24]=2[O:25][CH3:26])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Cl:57])C(=O)C1>CN(C=O)C.C(Cl)(Cl)(Cl)Cl.O>[Cl:57][CH2:2][CH:3]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]3[C:17]4[CH:30]=[CH:29][S:28][C:18]=4[C:19](=[O:27])[NH:20][C:21]=3[CH:22]=[CH:23][C:24]=2[O:25][CH3:26])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH3:4]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 67448518HCID 67448518, compound

Product 1

HCID 67448485HCID 67448485, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 86675469HCID 86675469, compoundSolvent

Procedure

To a mixture of N-(1-hydroxypropan-2-yl)-4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)benzenesulfonamide (140 mg, 0.30 mmol) and triphenylphosphine (160 mg, 0.62 mmol) in DMF/CCl4 (1 mL/3 mL) was added NCS (41 mg, 0.31 mmol) and the reaction mixture was stirred at room temperature for 15 h. The reaction mixture was diluted with water (ca. 20 mL), and extracted with DCM (1×50 mL). The extract was washed with water (2×20 mL), brine (1×10 mL), dried over sodium sulfate, and evaporated under vacuum. The residue was purified by flash chromatography to afford the desired product (100 mg, 74%) as light yellow solid; ESI MS m/z 464 [C21H19ClN2O4S+H]+

Workup

  1. extractionextracted with DCM (1×50 mL)
  2. washThe extract was washed with water (2×20 mL), brine (1×10 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated under vacuum
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6937f92735c7482a9b2cee99ed19fb78
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

Loading…