Diisopropylethylamine → HCID 58386576, compound

HRID 74634Notes

Reaction equation

HRID 74634 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH2:5][CH2:4]1.[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([C:29]([C:31]1[CH:36]=[C:35](Cl)[N:34]=[CH:33][N:32]=1)=[O:30])[CH2:24][CH2:23]2.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[N:25]([C:29]([C:31]1[N:32]=[CH:33][N:34]=[C:35]([N:3]3[CH2:4][CH2:5][CH:6]([N:9]4[C:17]5[C:12](=[N:13][CH:14]=[CH:15][CH:16]=5)[NH:11][C:10]4=[O:18])[CH2:7][CH2:8]3)[CH:36]=1)=[O:30])[CH2:24][CH2:23]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 58386763(5-Bromo-2,3-dihydroindol-1-yl)-(6-chloropyrimidin-4-yl)-methanone

Product 1

HCID 58386576HCID 58386576, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

70 mg (0.24 mmol) 1-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one dihydrochloride were added to 100 mg (0.30 mmol) (5-bromo-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 at 40° C. in the CAD.

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 at 40° C. in the CAD

Sources & evidence

ORD record
ord-01abe73218be43969707f51495941028
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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