Hydrochloric Acid → HCID 49803651, compound

HRID 1640282Notes

Reaction equation

HRID 1640282 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.Cl[C:21]1[N:26]=[CH:25][N:24]=[C:23]([C:27]([N:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:31][CH:30]2[CH2:38][CH3:39])=[O:28])[CH:22]=1.Cl>CC(O)C>[CH2:38]([CH:30]1[CH2:31][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:29]1[C:27]([C:23]1[N:24]=[CH:25][N:26]=[C:21]([NH:1][C:2]2[CH:3]=[C:4]3[C:17](=[CH:18][CH:19]=2)[CH2:16][C:6]2([C:14]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[NH:8][C:7]2=[O:15])[CH2:5]3)[CH:22]=1)=[O:28])[CH3:39]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 58117532(6-Chloro-pyrimidin-4-yl)-(2-ethyl-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 49803651HCID 49803651, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

103 mg (0.40 mmol) 5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, 113 mg (0.40 mmol) (6-chloro-pyrimidin-4-yl)-(2-ethyl-2,3-dihydro-indol-1-yl)-methanone and 13 μL of a 4 molar aqueous hydrochloric acid solution were added to 2.0 mL of 2-propanol and the mixture was refluxed for 2 h. Then the reaction mixture was evaporated down and purified by preparative HPLC-MS. The product-containing fractions were combined and the organic solvent was evaporated down. The residue was made alkaline with a 1N aqueous sodium hydroxide solution, the precipitate formed was suction filtered, washed with water and dried under HV.

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. customThen the reaction mixture was evaporated down
  3. custompurified by preparative HPLC-MS
  4. customthe organic solvent was evaporated down
  5. customthe precipitate formed
  6. filtrationfiltered
  7. washwashed with water
  8. customdried under HV

Sources & evidence

ORD record
ord-e553d57a41ce44cdbf3931f5d3218016
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

Loading…