HCID 90001316, compound → HCID 73506018, compound

HRID 1508308Notes

Reaction equation

HRID 1508308 reaction equation
[CH3:1][S:2]([CH2:5][C:6]([N:8]1[CH2:44][C:10]2([C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH2:23][C:22]([C:28]5[CH:33]=[C:32]([Cl:34])[C:31]([Cl:35])=[C:30]([Cl:36])[CH:29]=5)([C:24]([F:27])([F:26])[F:25])[N:21](C(OC(C)(C)C)=O)[N:20]=4)=[CH:16][CH:17]=3)[CH2:12][O:11]2)[CH2:9]1)=[O:7])(=[O:4])=[O:3]>O1CCOCC1>[ClH:34].[CH3:1][S:2]([CH2:5][C:6]([N:8]1[CH2:9][C:10]2([C:18]3[C:13](=[CH:14][C:15]([C:19]4[CH2:23][C:22]([C:28]5[CH:29]=[C:30]([Cl:36])[C:31]([Cl:35])=[C:32]([Cl:34])[CH:33]=5)([C:24]([F:26])([F:27])[F:25])[NH:21][N:20]=4)=[CH:16][CH:17]=3)[CH2:12][O:11]2)[CH2:44]1)=[O:7])(=[O:3])=[O:4]

Participants

3

Reactant 1

HCID 90001316HCID 90001316, compound

Product 1

HCID 73506018HCID 73506018, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

by dissolving tert-butyl 3-(1-(2-(methylsulfonyl)acetyl)-3′H-spiro[azetidine-3,1′-isobenzofuran]-5′-yl)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-1-carboxylate in dioxane (0.2M) and purged with HCl gas at 0° C. for 30 minutes. Reaction mixture was then stirred for 30 minutes at room temperature. After consumption of starting material, reaction mixture reaction mixture was concentrated in vacuo to get an orange semisolid. Crude was triturated with Chloroform:hexane (1:8) to afford title compound as off white solid. Yield: 105 mg (35%). 1H NMR (400 MHz, CDCl3) δ: 3.18 (s, 3H), 3.38 (d, J=17.2 Hz, 1H), 3.85-3.89 (m, 3H), 4.33 (d, J=9.8 Hz, 1H), 4.43 (d, J=11.08 Hz, 1H), 4.65 (s, 2H), 5.14 (s, 2H), 6.42 (s, 1H), 7.50-7.54 (m, 4H), 7.60-7.62 (d, J=7.8 Hz, 1H). LC-MS (m/z):=593.8 (M−H). HPLC 87.81%.

Workup

  1. custompurged with HCl gas at 0° C. for 30 minutes
  2. customReaction mixture
  3. customAfter consumption of starting material, reaction mixture reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customto get an orange semisolid
  6. customCrude was triturated with Chloroform:hexane (1:8)

Sources & evidence

ORD record
ord-32e801cd4832473a9cb9d457becef37c
Source dataset
uspto-grants-2015_12
Patent number
US09221835B2

Reaction notes

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