Hydrochloric Acid → ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

HRID 1506402Notes

Reaction equation

HRID 1506402 reaction equation
C1(C(=[N:14][C:15]([CH3:51])([CH2:21][CH2:22][C:23]2[CH:24]=[C:25]3[C:48](=[CH:49][CH:50]=2)[C:29]2=[N:30][O:31][C:32]([C:33]4[CH:34]=[N:35][N:36]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[C:37]=4[C:38]([F:41])([F:40])[F:39])=[C:28]2[CH2:27][CH2:26]3)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.Cl>C(OCC)C>[NH2:14][C:15]([CH3:51])([CH2:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:48](=[CH:49][CH:50]=1)[C:29]1=[N:30][O:31][C:32]([C:33]3[CH:34]=[N:35][N:36]([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:37]=3[C:38]([F:39])([F:40])[F:41])=[C:28]1[CH2:27][CH2:26]2)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86669897ethyl 2-(diphenylmethyleneamino)-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

Product 1

HCID 67170053ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoateYield 94.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred clear solution of ethyl 2-(diphenylmethyleneamino)-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (Preparation 50C, 120 mg, 0.174 mmol) in diethyl ether (3 mL) was added 4 N aqueous HCl (0.261 mL, 1.045 mmol) dropwise at room temperature. The reaction mixture was stirred at room temperature for 30 min. The ether layer was separated and the aqueous layer re-extracted with ether (2 mL). The aqueous solutions were basified with solid potassium carbonate and extracted with ethyl acetate (3×2 mL). The combined ethyl acetate extracts were dried over sodium sulfate and concentrated under reduced pressure to give ethyl 2-amino-2-methyl-4-(3-(1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate (86 mg, 0.164 mmol, 94% yield) as an yellow oil. The compound had an HPLC retention time=3.22 min (condition C); LC/MS M+1=525.5.

Workup

  1. customThe ether layer was separated
  2. extractionthe aqueous layer re-extracted with ether (2 mL)
  3. extractionextracted with ethyl acetate (3×2 mL)
  4. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa11bf9c7ef1408d89ecc4c0601db8b3
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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