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

HRID 1640268Notes

Reaction equation

HRID 1640268 reaction equation
Cl.Cl[C:3]1[N:8]=[CH:7][N:6]=[C:5]([C:9]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[CH2:13][CH:12]2[CH2:21][CH3:22])=[O:10])[CH:4]=1.[NH2:23][C:24]1[CH:25]=[C:26]2[C:39](=[CH:40][CH:41]=1)[CH2:38][C:28]1([C:36]3[C:31](=[N:32][CH:33]=[CH:34][CH:35]=3)[NH:30][C:29]1=[O:37])[CH2:27]2>CC(O)CCC>[CH2:21]([CH:12]1[CH2:13][C:14]2[C:19](=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[N:11]1[C:9]([C:5]1[N:6]=[CH:7][N:8]=[C:3]([NH:23][C:24]2[CH:25]=[C:26]3[C:39](=[CH:40][CH:41]=2)[CH2:38][C:28]2([C:36]4[C:31](=[N:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]2=[O:37])[CH2:27]3)[CH:4]=1)=[O:10])[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58117538(6-Chloro-pyrimidin-4-yl)-(2-ethyl-6-fluoro-2,3-dihydro-indol-1-yl)-methanoneHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 581174985-(6-(2-ethyl-6-fluorindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

63 μL (0.25 mmol) 4M aqueous hydrochloric acid were added to 516 mg (2.00 mmol) (6-chloro-pyrimidin-4-yl)-(2-ethyl-6-fluoro-2,3-dihydro-indol-1-yl)-methanone and 611 mg (2.00 mmol) 5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one in 10 mL of 2-pentanol. The reaction mixture was refluxed for 6 h. The reaction mixture was evaporated down using the rotary evaporator and the residue was taken up in DMF. The purification was carried out by preparative HPLC. The product fractions were combined and lyophilised.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customThe reaction mixture was evaporated down
  3. customthe rotary evaporator
  4. customThe purification

Sources & evidence

ORD record
ord-17ae6e4d9fd6465eb53b5bb82b17e301
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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