Diisopropylethylamine → 1-(6-(indoline-1-carbonyl)pyrimidin-4-yl)spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1640266Notes

Reaction equation

HRID 1640266 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:2]1=[O:15].Cl[C:17]1[N:22]=[CH:21][N:20]=[C:19]([C:23]([N:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26]2)=[O:24])[CH:18]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[N:25]1([C:23]([C:19]2[N:20]=[CH:21][N:22]=[C:17]([N:12]3[CH2:11][CH2:10][C:3]4([C:4]5[C:5](=[N:6][CH:7]=[CH:8][CH:9]=5)[NH:1][C:2]4=[O:15])[CH2:14][CH2:13]3)[CH:18]=2)=[O:24])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 56651734Spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-oneHCID 58117518(6-Chloropyrimidin-4-yl)-(2,3-dihydroindol-1-yl)-methanone

Product 1

HCID 426100731-(6-(indoline-1-carbonyl)pyrimidin-4-yl)spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

43 mg (0.21 mmol) spiro[piperidine-4,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one were added to 50 mg (0.19 mmol) (6-chloro-pyrimidin-4-yl)-(2,3-dihydro-indol-1-yl)-methanone and 52 μL (0.58 mmol) DIPEA in 5 mL DMF. The reaction mixture was stirred for 2 h at RT. The reaction mixture was evaporated down using the rotary evaporator and the residue was mixed with 20 mL water and stirred for 30 min at RT. The product precipitated was suction filtered, stirred with diisopropylether and isopropanol, suction filtered and dried.

Workup

  1. customThe reaction mixture was evaporated down
  2. customthe rotary evaporator
  3. additionthe residue was mixed with 20 mL water
  4. stirringstirred for 30 min at RT
  5. customThe product precipitated
  6. filtrationfiltered
  7. stirringstirred with diisopropylether and isopropanol, suction
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-0c73855477984bb493bcf676f4b1cebe
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

Loading…