Diisopropylethylamine → Ethyl 6-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate

HRID 74502Notes

Reaction equation

HRID 74502 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:13][CH2:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[NH:9][C:8]2=[O:18])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.Cl[C:29]1[N:34]=[CH:33][N:32]=[C:31]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:30]=1>CN(C=O)C.O>[O:18]=[C:8]1[N:7]([CH:4]2[CH2:3][CH2:2][N:1]([C:29]3[N:34]=[CH:33][N:32]=[C:31]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:30]=3)[CH2:6][CH2:5]2)[CH2:13][CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=2[NH:9]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 22756838Ethyl 6-chloropyrimidine-4-carboxylate

Product 1

HCID 58386764Ethyl 6-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

700 mg (2.85 mmol) 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one and 470 μL (2.73 mmol) DIPEA were added to 500 mg (2.68 mmol) ethyl 6-chloropyrimidine-4-carboxylate in 10 mL DMF and the reaction mixture was stirred for 1 h at RT. The reaction mixture was diluted with water and stirred for 30 min. The precipitate was suction filtered, washed with water and dried at 50° C. in the CAD.

Workup

  1. stirringstirred for 30 min
  2. filtrationfiltered
  3. washwashed with water
  4. customdried at 50° C. in the CAD

Sources & evidence

ORD record
ord-f545aef1561d43e38dac5fc0f87c4b86
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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