Triethylamine → HCID 136121607, compound

HRID 2079344Notes

Reaction equation

HRID 2079344 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 (1.15 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-cec3ad010bd9476eb0c54ede2208bdff
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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