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

HRID 1640269Notes

Reaction equation

HRID 1640269 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]=[CH:17][CH:18]=3)[CH2:13][CH:12]2[CH2:20][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>[CH2:20]([CH:12]1[CH2:13][C:14]2[C:19](=[CH:18][CH:17]=[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])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58117516(6-Chloro-pyrimidin-4-yl)-(2-propyl-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 498036525-(6-(2-propylindoline-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

12.5 μL (50 μmol) 4M aqueous hydrochloric acid were added to 103 mg (0.40 mmol) (6-chloro-pyrimidin-4-yl)-(2-propyl-2,3-dihydro-indol-1-yl)-methanone and 108 mg (0.36 mmol) 5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one in 2 mL 2-pentanol. The reaction mixture was refluxed for 2 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 2 h
  2. customThe reaction mixture was evaporated down
  3. customthe rotary evaporator
  4. customThe purification

Sources & evidence

ORD record
ord-5aefc3e395b44e2a942b661480a8732f
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

Loading…