Hydrochloric Acid → Ethyl 6-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylate

HRID 1640240Notes

Reaction equation

HRID 1640240 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1.Cl.[NH2:14][C:15]1[CH:16]=[C:17]2[C:30](=[CH:31][CH:32]=1)[CH2:29][C:19]1([C:27]3[C:22](=[N:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]1=[O:28])[CH2:18]2>CC(O)C>[O:28]=[C:20]1[NH:21][C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:27]2[C:19]21[CH2:18][C:17]1[C:30](=[CH:31][CH:32]=[C:15]([NH:14][C:2]3[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=3)[CH:16]=1)[CH2:29]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 22756838Ethyl 6-chloropyrimidine-4-carboxylateHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 58117511Ethyl 6-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.10 g (0.55 mmol) ethyl 6-chloropyrimidine-4-carboxylate and 13 μL (50 μmol) 4M HCl were added to 0.16 g (0.60 mmol) 5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one in 1.0 mL 2-propanol. The reaction mixture was refluxed for 2 h, then cooled to RT and the resulting solid was filtered off and dried.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. filtrationthe resulting solid was filtered off
  3. customdried

Sources & evidence

ORD record
ord-03b579ea4b1148ab84f4f6994fe3b816
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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