Diisopropylethylamine → 3-{1-[6-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one

HRID 74688Notes

Reaction equation

HRID 74688 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([F:19])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH:3]=1.[NH:20]1[CH2:25][CH2:24][CH:23]([N:26]2[CH2:31][C:30]3[CH:32]=[CH:33][CH:34]=[N:35][C:29]=3[NH:28][C:27]2=[O:36])[CH2:22][CH2:21]1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([C:8]([C:4]1[N:5]=[CH:6][N:7]=[C:2]([N:20]3[CH2:21][CH2:22][CH:23]([N:26]4[CH2:31][C:30]5[CH:32]=[CH:33][CH:34]=[N:35][C:29]=5[NH:28][C:27]4=[O:36])[CH2:24][CH2:25]3)[CH:3]=1)=[O:9])[CH2:11][CH2:12]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 222932273-Piperidin-4-yl-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-oneHCID 58117506(6-Chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

Product 1

HCID 426131433-{1-[6-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 mg (0.25 mmol) (6-chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone, 60 mg (0.26 mmol) 3-piperidin-4-yl-3,4-dihydro-1H-pyrido[2,3-d]pyrimidin-2-one and 52 μL (0.30 mmol) DIPEA in 5.0 mL DMF were shaken for 2 h at RT. Then the reaction mixture was poured onto water, stirred and the precipitate formed was suction filtered. This was washed with diisopropylether and dried.

Workup

  1. additionThen the reaction mixture was poured onto water
  2. customthe precipitate formed
  3. filtrationfiltered
  4. washThis was washed with diisopropylether
  5. customdried

Sources & evidence

ORD record
ord-fc3a0d84b8794562b3234f88fd7acdf2
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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