Triethylamine → HCID 136121607, compound

HRID 2062259Notes

Reaction equation

HRID 2062259 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][CH2:23][C@H:22]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[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[CH2:25][CH2:24][CH2:23][C@H:22]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:21]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 1514175Benzyl (3S)-piperidin-3-ylcarbamateHCID 1361050322-(4-Chloro-7-methylquinazolin-2-yl)-phenol

Product 1

HCID 136121607HCID 136121607, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-chloro-7-methylquinazolin-2-yl)phenol (115 g, 4.26 mmol) in CH2Cl2 (25 mL) at 0° C. under inert atmosphere was slowly added a solution of benzyl(S)-piperidin-3-ylcarbamate (1.0 g, 4.26 mmol) and triethylamine (1.18 mL, 8.52 mmol) in CH2Cl2 (10 mL). The reaction was allowed to warm to room temperature and was then quenched with water. The mixture was extracted with CH2Cl2 and the organic layers were combined, dried over MgSO4, and concentrated to obtain benzyl(S)-1-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperidin-3-ylcarbamate (2.03 g). This material was used without further purification. LC/MS: m/z 469.1 (M+H)+ at 2.86 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA))

Workup

  1. customwas then quenched with water
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a0c4c67d5a2943749f72dda757cc9d67
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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