Hydrochloric Acid → HCID 178506082, compound

HRID 1497236Notes

Reaction equation

HRID 1497236 reaction equation
Cl[C:2]1[C:11]([C:12]2[NH:16][N:15]=[N:14][N:13]=2)=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:23]([F:26])([F:25])[F:24])[CH:8]=2)[N:3]=1.[NH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C(N(CC)CC)C.Cl>CC(N(C)C)=O>[C:17]1([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:23]([F:26])([F:25])[F:24])[CH:8]=3)[N:3]=[C:2]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C:11]=2[C:12]2[NH:16][N:15]=[N:14][N:13]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 8471TriethylamineHCID 178506080HCID 178506080, compound

Product 1

HCID 178506082HCID 178506082, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-4-phenyl-3-(1H-tetrazol-5-yl)-6-trifluoromethyl-quinoline (105 mg, 279 μmol), piperidine (47.6 mg, 55.3 μl, 559 μmol) and triethylamine (84.8 mg, 117 μl, 838 μmol) in DMA (2 ml) was heated to 100° C. in a sealed tube. After 4 h 0.1N HCl was added at room temperature and the mixture was extracted with EtOAc. The combined organic layers were washed with 0.1N HCl and brine and dried with Na2SO4. The remaining brown oil was purified by chromatography (silica gel, DCM/MeOH 98:2 to 95:5). The product fractions were concentrated and the remaining solid was dissolved in EtOAc, filtered through silica gel and evaporated. The remaining residue was finally purified by preparative thin-layer chromatography (DCM/MeOH 95:5) to obtain the title compound (22 mg, 18%) as light yellow solid. MS (ESI): 425.4 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic layers were washed with 0.1N HCl and brine
  3. dry with materialdried with Na2SO4
  4. customThe remaining brown oil was purified by chromatography (silica gel, DCM/MeOH 98:2 to 95:5)
  5. concentrationThe product fractions were concentrated
  6. dissolutionthe remaining solid was dissolved in EtOAc
  7. filtrationfiltered through silica gel
  8. customevaporated
  9. customThe remaining residue was finally purified by preparative thin-layer chromatography (DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-94d7cee912bb44da9788857304709a7e
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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