Diisopropylethylamine → 3-(2-methoxy-pyrimidin-5-yl)-2-{[4-(2-oxo-1,4-dihydro-2H-quinazolin-3-yl)-piperidine-1-carbonyl]-amino}-propionic acid methyl ester

HRID 2250221Notes

Reaction equation

HRID 2250221 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])=[N: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])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 676246Di(succinimido) carbonateHCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 59639681Methyl 2-amino-3-(2-methoxypyrimidin-5-yl)propanoate

Product 1

HCID 588642893-(2-methoxy-pyrimidin-5-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-(2-methoxy-pyrimidin-5-yl)-propionic acid methyl ester (125 mg) and diisopropylethylamine (0.3 mL) in methylene chloride (2 mL, 0° C.) was added N,N′-disuccinimidyl carbonate (155 mg). After 30 min, 3-piperidin-4-yl-3,4-dihydro-1H-quinazolin-2-one (120 mg) in methylene chloride (2 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 99 mg (36%). Mass spec.: 469.10 (MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by prep HPLC
  3. customto give 99 mg (36%)

Sources & evidence

ORD record
ord-f640679e58d042bfb71ab72ddd339484
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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