Hydrochloric Acid → HCID 58993550, compound

HRID 391469Notes

Reaction equation

HRID 391469 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=2)[CH2:10][O:11][CH2:12][C:13]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[N:5][N:4]=[N:3]1.Cl>C(OCC)(=O)C>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:32]=[C:33]([C:35]([F:37])([F:38])[F:36])[CH:34]=2)[CH2:10][O:11][CH2:12][C:13]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[N:5][N:4]=[N:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58993518HCID 58993518, compound

Product 1

HCID 58993550HCID 58993550, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-((3-(1-methyl-1H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (7.0 mg, 0.01 mmol) was dissolved in a minimum amount of ethyl acetate, followed by addition of 4 N hydrochloric acid (0.5 mL). The mixture was stirred under nitrogen for 1 h. After removing the solvents, the crude mixture was precipitated in diethyl ether and filtered to afford 4.0 mg (88%). 1H-NMR (CDCl3, 500 MHz) δ 7.86 (s, 1H), 7.57 (s, 1H), 7.48 (s, 1H), 7.34 (s, 1H), 7.33 (s, 1H), 7.27-7.29 (m, 2H), 7.20 (m, 1H), 4.49 (s, 2H), 4.06 (s, 3H), 3.48 (s, 2H), 2.93-2.96 (m, 2H), 2.74-2.77 (m, 2H), 2.20-2.22 (m, 2H), 1.89-1.94 (m, 2H). Mass spec.: 432.20 (MH)+. Accurate mass spec.: m/z 432.1994 [MH]+, Δ=4.4 ppm.

Workup

  1. customAfter removing the solvents
  2. customthe crude mixture was precipitated in diethyl ether
  3. filtrationfiltered
  4. customto afford 4.0 mg (88%)

Sources & evidence

ORD record
ord-2078b94cdf234ec1a3e88a1fb80c42a8
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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