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Diisopropylethylamine → 1-{1-[6-(5-Chloro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 74633
Notes
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Reaction equation

HRID 74633 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:16])[CH2:3][CH2:2]1.[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([C:27]([C:29]1[CH:34]=[C:33](Cl)[N:32]=[CH:31][N:30]=1)=[O:28])[CH2:22][CH2:21]2.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[N:23]([C:27]([C:29]1[N:30]=[CH:31][N:32]=[C:33]([N:1]3[CH2:2][CH2:3][CH:4]([N:7]4[C:15]5[C:10](=[N:11][CH:12]=[CH:13][CH:14]=5)[NH:9][C:8]4=[O:16])[CH2:5][CH2:6]3)[CH:34]=1)=[O:28])[CH2:22][CH2:21]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22293182Bms-973013HCID 58117515(5-Chloro-2,3-dihydroindol-1-yl)-(6-chloropyrimidin-4-yl)-methanone

Product 1

HCID 583866221-{1-[6-(5-Chloro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

80 mg (0.27 mmol) 1-piperidin-4-yl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (dihydrochloride) were added to 100 mg (0.34 mmol) (5-chloro-2,3-dihydroindol-1-yl)-(6-chloropyrimidin-4-yl)-methanone and 100 μL (0.58 mmol) DIPEA in 10 mL DMF. The reaction mixture was stirred for 22 h at RT and then evaporated down i. vac. The residue was combined with 20 mL water and stirred for 30 min at RT. The precipitated product was suction filtered. The purification was carried out using a silica gel column. The product fractions were combined and the solvent was eliminated using the rotary evaporator. The residue was stirred with water, suction filtered and dried.

Workup

  1. customevaporated down i
  2. stirringstirred for 30 min at RT
  3. customThe purification
  4. customthe rotary evaporator
  5. stirringThe residue was stirred with water, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-3b2d427af17f47889012c9eb56d19d5e
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829006B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes