Trifluoroacetic acid → HCID 136104957, compound

HRID 2062288Notes

Reaction equation

HRID 2062288 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:17]=[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24]C(=O)OC(C)(C)C)[CH2:20][CH2:19]2)[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=2)[N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][CH:21]1[CH2:22][CH2:23][N:18]([C:16]2[C:15]3[C:10](=[CH:11][C:12]([CH3:32])=[CH:13][CH:14]=3)[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[N:17]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136121342HCID 136121342, compound

Product 1

HCID 136104957HCID 136104957, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-4-ylcarbamate (3.21 g, 7.39 mmol) was dissolved in CH2Cl2 (55 ml). TFA (50 ml) was added and the reaction was stirred for 1 hour. After evaporating the solvents in vacuo, the crude material was diluted with CH2Cl2 and neutralized with a 1 N NaOH solution. The layers were separated, and the aqueous layer was extracted three times with CH2Cl2 (30 ml). The combined organic layers were dried over MgSO4, filtered, and concentrated to give 2-(4-(4-aminopiperidin-1-yl)-7-methylquinazolin-2-yl)phenol as a yellow solid (2.06 g, 83%). LC/MS: m/z 335.3 (M+H)+ at 1.42 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customAfter evaporating the solvents in vacuo
  2. additionthe crude material was diluted with CH2Cl2
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted three times with CH2Cl2 (30 ml)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5efa9e226b7f40a788e9db8504e88a13
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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