Hydrochloric Acid → HCID 86670535, compound

HRID 1258012Notes

Reaction equation

HRID 1258012 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([C:13]2([C:38]([F:41])([F:40])[F:39])[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C:23]3([CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]3)[NH:22][C:21]4=[O:37])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl>CO>[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([C:13]2([C:38]([F:39])([F:40])[F:41])[O:17][N:16]=[C:15]([C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C:23]3([CH2:27][NH:28][CH2:29]3)[NH:22][C:21]4=[O:37])[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86670536HCID 86670536, compound

Product 1

HCID 86670535HCID 86670535, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A 100 mL vial equipped with stir bar was charged with tert-butyl 5′-(5-(3,5-bis(trifluoromethyl)phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-3′-oxospiro[azetidine-3,1′-isoindoline]-1-carboxylate (Preparation 21, 240 mg, 0.4 mmol) and anhydrous methanol (25 mL). A methanolic solution of HCl (1 mL of a 1.25M solution) was added and the reaction was heated to 65° C. for 6 hours. The reaction was cooled and concentrated under vacuum. The residue was rinsed with diethyl ether, concentrated under vacuum, and subsequently placed under high vacuum for 1 hour to afford the intermediate (216 mg, 95%) as an HCl salt. m/z (CI) 524 [M+H]+.

Workup

  1. customA 100 mL vial equipped
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated under vacuum
  4. washThe residue was rinsed with diethyl ether
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9a005ddd422647039b0b7033ad8f8e65
Source dataset
uspto-grants-2013_06
Patent number
US08466115B2

Reaction notes

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