Bis-(1H-imidazol-2-YL)-methanone → 3-(6-benzyloxy-pyridin-3-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester

HRID 1177749Notes

Reaction equation

HRID 1177749 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([NH2:20])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:11]=1.[C:22](C1NC=CN=1)(C1NC=CN=1)=[O:23].[NH:34]1[CH2:39][CH2:38][CH:37]([N:40]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[NH:42][C:41]2=[O:50])[CH2:36][CH2:35]1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[CH:4]([NH:20][C:22]([N:34]1[CH2:35][CH2:36][CH:37]([N:40]2[CH2:49][C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[NH:42][C:41]2=[O:50])[CH2:38][CH2:39]1)=[O:23])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 588642862-Amino-3-(6-benzyloxy-pyridin-3-yl)-propionic acid methyl ester

Product 1

HCID 588642363-(6-benzyloxy-pyridin-3-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-amino-3-(6-benzyloxy-pyridin-3-yl)-propionic acid methyl ester (60 mg, 0.21 mmol) in methylene chloride (1 mL, 0° C.) was added carbonyl diimidazole (34 mg, 1.0 equiv.). After 15 min, a solution of 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (58 mg, 1.2 equiv.) in methylene chloride (0.5 mL) was added via canula. The ice bath was removed and stirring continued overnight. The reaction was concentrated and purified by column chromatography to give 59 mg (52%). Mass spec.: 544.49 (MH)+.

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction was concentrated
  3. custompurified by column chromatography
  4. customto give 59 mg (52%)

Sources & evidence

ORD record
ord-16f606d6f3d04bbc867091b57c582b36
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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