Nipecotic Acid → HCID 136121350, compound

HRID 2079343Notes

Reaction equation

HRID 2079343 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[N:3]=1.C(N(CC)CC)C.[NH:27]1[CH2:32][CH2:31][CH2:30][CH:29]([C:33]([OH:35])=[O:34])[CH2:28]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:4]1[N:3]=[C:2]([N:27]2[CH2:32][CH2:31][CH2:30][CH:29]([C:33]([OH:35])=[O:34])[CH2:28]2)[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 4

HCID 4498Nipecotic AcidHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

Product 1

HCID 136121350HCID 136121350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (0.449 mg, 1.66 mmol) in CH2Cl2 was added 5 equivalents of triethylamine followed by the addition of piperidine-3-carboxylic acid as a TFA salt. The reaction was stirred for 2 hours and quenched with water. The layers were separated, and the organic extracts were dried over MgSO4, filtered, and concentrated to give 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidine-3-carboxylic acid which was used without further purification. LC/MS: m/z 364.3 (M+H)+ at 2.22 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customquenched with water
  2. customThe layers were separated
  3. dry with materialthe organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-858e26e38aed40d8ad5828734c0873d0
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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