Dimethylformamide → HCID 71262406, compound

HRID 540264Notes

Reaction equation

HRID 540264 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OC(F)(F)F)[CH:10]=2)[N:5]=[C:4]([N:17]2[CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[S:20](=[O:29])(=[O:28])[CH2:19][CH2:18]2)[CH:3]=1.[CH:30]([C@@H:32]1[CH2:36][O:35][C:34]([CH3:38])([CH3:37])[N:33]1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH2:31].[CH2:46](N(CC)CC)C.CN(C)C=O>CC(P(C(C)(C)C)C(C)(C)C)(C)C.CC(P(C(C)(C)C)C(C)(C)C)(C)C.[Pd].O>[O:28]=[S:20]1(=[O:29])[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH2:23][N:17]([C:4]2[CH:3]=[C:2](/[CH:31]=[CH:30]/[C@@H:32]3[CH2:36][O:35][C:34]([CH3:38])([CH3:37])[N:33]3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:46])[CH:10]=3)[N:5]=2)[CH2:18][CH2:19]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10878894(R)-N-BOC-2,2-DIMETHYL-4-VINYLOXAZOLIDINEHCID 712545694-(4-Chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

Product 1

HCID 71262406HCID 71262406, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 2734558Bis(tri-tert-butylphosphine)palladium(0)CatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a vial containing a mixture of 4-(4-chloro-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (200 mg, 0.536 mmol, prepared in analogy to 4-(4-chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide in Example 17-1), tert-butyl (4R)-4-ethenyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (146 mg, 0.643 mmol), triethylamine (0.5 mL) and N,N-dimethylformamide (1 mL), which was evacuated and filled with argon, di(tri-tert-butylphosphine)palladium(0) (13.7 mg, 0.0268 mmol) was added. The vial was caped and heated at 110° C. for 30 minutes under microwave irradiation. The reaction mixture was poured into water (30 mL) and extracted with ethyl acetate (20 mL×3). The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 50% ethyl acetate in hexanes) to afford 180 mg of the desired product as a white solid (yield was 60%).

Workup

  1. additionTo a vial containing
  2. customwas evacuated
  3. additionwas added
  4. customThe vial was caped
  5. extractionextracted with ethyl acetate (20 mL×3)
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (eluting with 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-db38b03239a1496a9bbc0aaf5866e5e9
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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