Hydrochloric Acid → HCID 117668024, compound

HRID 1052962Notes

Reaction equation

HRID 1052962 reaction equation
[CH:1]1([C@:7]2([NH:31]S(C(C)(C)C)=O)[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:16]4[C:17]([CH3:22])=[N:18][O:19][C:20]=4[CH3:21])[CH:14]=3)[N:9](C(OC(C)(C)C)=O)[C:8]2=[O:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>O1CCOCC1>[NH2:31][C@@:7]1([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[C:17]([CH3:22])=[N:18][O:19][C:20]=3[CH3:21])[CH:14]=2)[NH:9][C:8]1=[O:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118691574HCID 118691574, compound

Product 1

HCID 117668024HCID 117668024, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (S)-tert-butyl 3-cyclohexyl-3-(1,1-dimethylethylsulfinamido)-5-(3,5-dimethyl-isoxazol-4-yl)-2-oxoindoline-1-carboxylate (53 mg, 0.1 mmol) in 2 mL of dioxane was added, a HCl saturated dioxane solution (1.0 mmol) at room temperature. The reaction mixture was stirred for 15 min. The reaction was quenched with 6 mL of aqueous NaHCO3, and the organic phase was extracted with CH2Cl2, dried, and evaporated under reduced pressure to afford pure (S)-3-amino-3-cyclohexyl-5-(3,5-dimethylisoxazol-4-yl)indolin-2-one (21 mg, 65%) as a solid. 1H NMR (400 MHz, DMSO-d6): δH 10.32 (s, 1H), 7.17-7.19 (m, 2H), 6.88 (d, J=8.8 Hz, 1H), 2.39 (s, 3H), 2.21 (s, 3H), 1.90-1.93 (m, 1H), 1.53-1.63 (m, 5H), 0.95-1.11 (m, 4H), 0.68-0.72 (m, 1H). MS (ESI) m/e [M+1]+ 326. MS (ESI) m/e [M+1]+ 326.

Workup

  1. customat room temperature
  2. customThe reaction was quenched with 6 mL of aqueous NaHCO3
  3. extractionthe organic phase was extracted with CH2Cl2
  4. customdried
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-277d3e1e210a494a8dc0690c950ecb03
Source dataset
uspto-grants-2016_07
Patent number
US09393232B2

Reaction notes

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