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

HRID 2355906Notes

Reaction equation

HRID 2355906 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH2:14])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1.C(N(C(C)C)CC)(C)C.C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)[C:27](=[O:28])C1.[NH:43]1[CH2:48][CH2:47][CH:46]([N:49]2[CH2:58][C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[NH:51][C:50]2=[O:59])[CH2:45][CH2:44]1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:14][C:27]([N:43]1[CH2:44][CH2:45][CH:46]([N:49]2[CH2:58][C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[NH:51][C:50]2=[O:59])[CH2:47][CH2:48]1)=[O:28])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 676246Di(succinimido) carbonateHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 59639680(+)-2-Amino-3-(6-methoxy-pyridin-3-yl)-propionic acid methyl ester

Product 1

HCID 596396773-(6-methoxy-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 solution of 2-amino-3-(6-methoxy-pyridin-3-yl)-propionic acid methyl ester (130 mg) and diisopropylethylamine (0.3 mL) in methylene chloride (2 mL, 0° C.) was added N,N′-disuccinimidyl carbonate (158 mg). After 30 min, 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (120 mg) in methylene chloride (1 mL) was added via canula. The reaction was warmed to room temperature and stirred overnight. The reaction was concentrated and purified by prep HPLC to give 160 mg (55%). Mass spec.: 468.19 (MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by prep HPLC
  3. customto give 160 mg (55%)

Sources & evidence

ORD record
ord-4c7ec1c1616b4f2686f19b4c8cf5070e
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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