Hydrochloric Acid → (+/-)-2-(1-Amino-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

HRID 2174087Notes

Reaction equation

HRID 2174087 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([C:20]3[C:28]([O:29][CH3:30])=[CH:27][C:26]([CH3:31])=[C:25]4[C:21]=3[CH:22]=[CH:23][N:24]4C(OC(C)(C)C)=O)([NH:13]S(C(C)(C)C)=O)[CH3:12])=[N:8][C:7]=2[CH:39]=1)#[N:2].Cl>O1CCOCC1>[NH2:13][C:11]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:39][C:7]=2[N:8]=1)([C:20]1[C:28]([O:29][CH3:30])=[CH:27][C:26]([CH3:31])=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2)[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86701723tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Product 1

HCID 86701722(+/-)-2-(1-Amino-1-(5-methoxy-7-methyl-1H-indol-4-yl)ethyl)benzo[d]oxazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)-1-(1,1-dimethylethylsulfinamido)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (120 mg, 0.218 mmol) in dioxane (1 mL) was added 4M HCl in dioxane (2.2 mL, 8.72 mmol) and the mixture was stirred at 60° C. After 2 hours the reaction was cooled in an ice bath and quenched with 30% aq. NH4OH (2.18 mL). Water was added, the layers were separated and the aqueous layer was extracted with EtOAc, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-100% EtOAc:Heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.92 (br. s., 1H) 8.29 (dd, J=1.39, 0.88 Hz, 1H) 7.72-7.85 (m, 2H) 7.28 (t, J=2.84 Hz, 1H) 7.05-7.16 (m, 1H) 6.64 (s, 1H) 3.19 (s, 3H) 2.59 (br. s., 2H) 2.43 (s, 3H) 1.90 (s, 3H). HRMS calcd. for C20H18N4O2 (M+H)+ 347.1503. found 347.1486.

Workup

  1. temperatureAfter 2 hours the reaction was cooled in an ice bath
  2. customquenched with 30% aq. NH4OH (2.18 mL)
  3. additionWater was added
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by flash chromatography (0-100% EtOAc:Heptanes)

Sources & evidence

ORD record
ord-d480424db5674bf0b7c23d6c4b41c172
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…