Water → HCID 68245115, compound

HRID 515243Notes

Reaction equation

HRID 515243 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:29])=[C:9]([C:11]2[N:16]=[C:15]3[N:17]([CH3:28])[S:18](=[O:27])(=[O:26])[N:19]([CH2:20][CH:21]4[CH2:23][C:22]4([F:25])[F:24])[C:14]3=[CH:13][CH:12]=2)[CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1.CCOC(C)=O>[F:25][C:22]1([F:24])[CH2:23][CH:21]1[CH2:20][N:19]1[C:14]2[C:15](=[N:16][C:11]([C:9]3[CH:10]=[C:5]([CH2:4][NH2:1])[CH:6]=[CH:7][C:8]=3[CH3:29])=[CH:12][CH:13]=2)[N:17]([CH3:28])[S:18]1(=[O:26])=[O:27]

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86687906HCID 86687906, compound

Product 1

HCID 68245115HCID 68245115, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-[5-(azidomethyl)-2-methylphenyl]-1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridine 2,2-dioxide (44-1) (480 mg, 1.1 mmol, 1.0 eq) in THF (6.7 mL) was added triphenylphosphine (600 mg, 2.3 mmol, 2.0 eq) followed by water (0.31 mL, 17.1 mmol, 15 eq). The reaction mixture stirred at ambient temperature overnight and was then diluted with EtOAc (100 mL), washed with sodium bicarbonate (4×10 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (24 g SiO2, 20-100% EtOAc in hexanes) to afford 1-(3-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4-b]pyridin-5-yl}-4-methylphenyl)methanamine (44-2). HRMS m/z (M+H) 395.1348 found, 395.1348 required.

Workup

  1. washwashed with sodium bicarbonate (4×10 mL) and brine (20 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography (24 g SiO2, 20-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e2e19d98026b43f09703faba4beddd62
Source dataset
uspto-grants-2015_08
Patent number
US09108937B2

Reaction notes

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