Hydrochloric Acid → HCID 58117496, compound

HRID 1640274Notes

Reaction equation

HRID 1640274 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][C:34]([F:38])=[CH:35][CH:36]=3)[CH2:31][CH2:30]2)=[O:28])[CH:22]=1.Cl.CC(O)C>C(OCC)C>[F:38][C:34]1[CH:33]=[C:32]2[C:37](=[CH:36][CH:35]=1)[N:29]([C:27]([C:23]1[N:24]=[CH:25][N:26]=[C:21]([NH:1][C:2]3[CH:3]=[C:4]4[C:17](=[CH:18][CH:19]=3)[CH2:16][C@:6]3([C:14]5[C:9](=[N:10][CH:11]=[CH:12][CH:13]=5)[NH:8][C:7]3=[O:15])[CH2:5]4)[CH:22]=1)=[O:28])[CH2:30][CH2:31]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 53260812(R)-5-Amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-oneHCID 58117506(6-Chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

Product 1

HCID 58117496HCID 58117496, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.10 g (0.40 mmol) (R)-5-amino-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, 0.11 g (0.40 mmol) (6-chloro-pyrimidin-4-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone and 13 μL of a 4 molar aqueous hydrochloric acid solution were added to 2.0 mL 2-propanol and the mixture was refluxed for 4 h. Then the reaction mixture was diluted with diethyl ether, suction filtered and washed with diethyl ether. The precipitate was dissolved in DMF 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 4 h
  2. filtrationfiltered
  3. washwashed with diethyl ether
  4. dissolutionThe precipitate was dissolved in DMF
  5. custompurified by preparative HPLC-MS
  6. customthe organic solvent was evaporated down
  7. customthe precipitate formed
  8. filtrationfiltered
  9. washwashed with water
  10. customdried under HV

Sources & evidence

ORD record
ord-453cb9ff04424004a1559fb40ab554c1
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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