Diisopropylethylamine → 5-(2-(2-ethyl-6-fluorindoline-1-carbonyl)pyridin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1640290Notes

Reaction equation

HRID 1640290 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:18][C:17]1[C:12](=[CH:13][CH:14]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][N:23]=[C:22]([C:26](O)=[O:27])[CH:21]=3)[CH:16]=1)[CH2:11]2.[CH2:29]([CH:31]1[CH2:39][C:38]2[C:33](=[CH:34][C:35]([F:40])=[CH:36][CH:37]=2)[NH:32]1)[CH3:30].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH2:29]([CH:31]1[CH2:39][C:38]2[C:33](=[CH:34][C:35]([F:40])=[CH:36][CH:37]=2)[N:32]1[C:26]([C:22]1[CH:21]=[C:20]([NH:19][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[CH2:11][C:3]2([C:4]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[NH:10][C:2]2=[O:1])[CH2:18]3)[CH:25]=[CH:24][N:23]=1)=[O:27])[CH3:30]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 581175174-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)picolinic acidHCID 581175392-ethyl-6-fluoro-2,3-dihydro-1H-indole

Product 1

HCID 498013765-(2-(2-ethyl-6-fluorindoline-1-carbonyl)pyridin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

186 mg (0.50 mmol) 4-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)picolinic acid, 220 mg (0.60 mmol) 2-ethyl-6-fluoro-2,3-dihydro-1H-indole, 0.26 mL (1.5 mmol) DIPEA and 0.18 g (0.55 mmol) TBTU in 5.0 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and the organic solvent was evaporated down. The aqueous residue was made alkaline with 1N aqueous sodium hydroxide solution, the precipitate formed was suction filtered, washed with water and dried under HV.

Workup

  1. customThe purification
  2. customthe organic solvent was evaporated down
  3. customthe precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. customdried under HV

Sources & evidence

ORD record
ord-a643f4faeee54105abbaf11f5eaed78d
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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