Hydrochloric Acid → HCID 70656091, compound

HRID 872925Notes

Reaction equation

HRID 872925 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[CH:25]=[C:24]([CH2:26][CH2:27][O:28]C4CCCCO4)[O:23][N:22]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[CH:25]=[C:24]([CH2:26][CH2:27][OH:28])[O:23][N:22]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 671725183-Isoxazolecarboxamide, N-[(1S)-2-[3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl]-1-methylethyl]-5-[2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl]-

Product 1

HCID 70656091HCID 70656091, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into a solution containing N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)isoxazole-3-carboxamide (0.04 g, 0.083 mmol) and ethanol (4 ml), hydrogen chloride, 10% in EtOH (0.5 ml, 1.350 mmol) was added. The resulting mixture was stirred for 2 h at RT. The mixture was evaporated, 2 ml of diethyl ether was added and stirred. The precipitated product was filtered and washed with cold heptane. The product was pure enough without further purifications. Yield 85%. 1H-NMR (400 MHz; DMSO-d6): δ 1.16 (d, 3H), 2.92 (t, 2H), 3.69 (t, 2H), 4.29-4.34 (m, 2H), 4.41-4.50 (m, 1H), 6.51-6.53 (m, 1H), 6.94 (d, 1H), 7.82 (d, 1H), 7.92 (dd, 1H), 7.97 (dd, 1H), 8.09 (d, 1H), 8.73 (d, 1H).

Workup

  1. additionwas added
  2. customThe mixture was evaporated
  3. addition2 ml of diethyl ether was added
  4. stirringstirred
  5. filtrationThe precipitated product was filtered
  6. washwashed with cold heptane

Sources & evidence

ORD record
ord-26716191b9c14d2890239d70a50ee8bf
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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