Triethylamine → HCID 136121342, compound

HRID 2062287Notes

Reaction equation

HRID 2062287 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.[NH:20]1[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]1.C(N(CC)CC)C>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:20]2[CH2:21][CH2:22][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])[CH2:24][CH2:25]2)[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

Product 1

HCID 136121342HCID 136121342, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (2.0 g, 7.38 mmol) in CH2Cl2 (25 ml) at 0° C. under an N2 atmosphere was added dropwise a solution of tert-butyl piperidin-4-ylcarbamate (1.92 g, 9.6 mmol) in CH2Cl2 (10 ml) and triethylamine (2.0 ml, 14.76 mmol). The reaction was stirred for 6 hours, then it was quenched with water (25 ml), and the layers were separated. The aqueous phase was extracted twice with CH2Cl2 (10 ml), and the combined organic layers were dried over MgSO4, filtered, and concentrated to give tert-butyl 1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-4-ylcarbamate as a yellow solid (3.24 g, 100%). LC/MS: m/z 435.3 (M+H)+ at 2.79 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customit was quenched with water (25 ml)
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted twice with CH2Cl2 (10 ml)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-85495e5ff8254b1482bdc30024b7898c
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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