Hydrochloric Acid → HCID 58993657, compound

HRID 391468Notes

Reaction equation

HRID 391468 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([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:3]1.Cl>C(OCC)(=O)C>[CH3:1][N:2]1[N:6]=[N:5][C:4]([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:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58993704HCID 58993704, compound

Product 1

HCID 58993657HCID 58993657, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-((3-(2-methyl-2H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (48.0 mg, 0.09 mmol) was dissolved in a minimum amount of ethyl acetate, followed by addition of 4 N hydrochloric acid (1 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 26.0 mg (67%) as a white powder. 1H-NMR (CDCl3, 300 MHz) δ 8.23 (s, 1H), 8.10 (s, 1H), 7.40 (s, 1H), 7.28-7.36 (m, 4H), 7.20 (m, 1H), 4.41 (s, 2H), 4.38 (s, 3H), 3.44 (s, 2H), 2.86-2.93 (m, 2H), 2.69-2.77 (m, 2H), 2.16-2.20 (m, 2H), 1.83-1.96 (m, 2H). 13C-NMR (CDCl3, 76 MHz) δ 164.0, 143.4, 141.0, 131.4 (q, J=32.8 Hz), 128.3, 128.0, 127.0, 126.1, 135.5, 124.0 (q, J=213.8 Hz), 122.6, 121.9, 79.9, 72.0, 42.3, 41.7, 39.5, 32.9. Mass spec.: 432.20 (MH)+. Accurate mass spec.: m/z 432.1994 [MH]+, Δ=4.0 ppm.

Workup

  1. customAfter removing the solvents
  2. customthe crude mixture was precipitated in diethyl ether
  3. filtrationfiltered
  4. customto afford 26.0 mg (67%) as a white powder

Sources & evidence

ORD record
ord-cfc2e4cac8e047ceaad56b3f13564032
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

Loading…