Hydrochloric Acid → HCID 66615865, compound

HRID 1404258Notes

Reaction equation

HRID 1404258 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.Cl[C:26]1[O:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.Cl>CC(O)(C)C.COCCOC.O1CCOCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:26]4[O:27][C:28]5[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=5[N:30]=4)=[CH:19][N:18]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 119862-ChlorobenzoxazoleHCID 66615773Methyl 2-((1r,4r)-4-(4-(5-aminopyridin-2-yl)phenyl)cyclohexyl)acetate

Product 1

HCID 66615865HCID 66615865, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 86596206tert butanol DMESolvent

Conditions

Temperature
120 °C

Procedure

65 mg of {4-[4-(5-Amino-pyridin-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester and 0.3 Ml of 2-chlorobenzoxazole were dissolved in 1.5 Ml of t-BuOH/DME (1:1) in a 5 Ml microwave tube with a stirring bar. 0.1 Ml of 4N-HCl in dioxane was added and the reaction vessel was sealed and heated at 120° C. for 2 hours by microwave. The reaction was diluted with ethyl acetate and the resulting precipitates were filtered and washed with ethyl acetate. The filter cake was dried by air in the suction funnel and analyzed by 1H-NMR (400 MHz, DMSO-d6) ppm 1.2 (s, 3 H) 1.5 (s, 2 H) 1.8 (s, 6 H) 2.3 (d, J=6.8 Hz, 2 H) 3.6 (s, 4 H) 7.2 (m, 1 H) 7.3 (m, 1 H) 7.3 (d, J=8.3 Hz, 2 H) 7.5 (d, J=13.9 Hz, 2 H) 8.0 (m, 3 H) 8.4 (m, 1 H) 8.9 (d, J=2.3 Hz, 1 H) 11.0 (s, 1 H); (M+H)+ 442.2.

Workup

  1. customthe reaction vessel was sealed
  2. customthe resulting precipitates
  3. filtrationwere filtered
  4. washwashed with ethyl acetate
  5. customThe filter cake was dried by air in the suction funnel

Sources & evidence

ORD record
ord-4ca2a4990cdf4822bcc7569d3ac72263
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

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