Hydrochloric Acid → HCID 68763641, compound

HRID 529091Notes

Reaction equation

HRID 529091 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]3)[CH2:9][N:8]([C:23]3[C:24]4[C@H:31]([CH3:32])[CH2:30][CH2:29][C:25]=4[N:26]=[CH:27][N:28]=3)[C:5]2=[CH:6][CH:7]=1.[ClH:33]>C(Cl)Cl.O1CCOCC1>[ClH:33].[ClH:33].[F:1][C:2]1[CH:3]=[C:4]2[C@:10]3([CH2:15][CH2:14][CH2:13][NH:12][CH2:11]3)[CH2:9][N:8]([C:23]3[C:24]4[C@H:31]([CH3:32])[CH2:30][CH2:29][C:25]=4[N:26]=[CH:27][N:28]=3)[C:5]2=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68796762HCID 68796762, compound

Product 1

HCID 68763641HCID 68763641, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 5-fluoro-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3′-piperidine]-1′-carboxylate (0.110 g, 0.251 mmol) in DCM (3 mL) was added 4N HCl in dioxane (0.63 mL). The reaction mixture was stirred overnight and then filtered. Evaporation of the mother liquid gave (R)-4-((S)-5-fluorospiro[indoline-3,3′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine dihydrochlorid. LCMS (APCI+) m/z 339 [M+H]+; Rt=2.29 min. The solid collected by filtration was suspended in 5:1 MeCN/MeOH (1 mL) and heated at reflux for about 5 minutes. After cooling, the precipitated solid was filtered and dried in air to give (R)-4-((R)-5-fluorospiro[indoline-3,3′-piperidine]-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine dihydrochloride. LCMS (APCI+) m/z 339 [M+H]+; Rt=2.31 min.

Workup

  1. filtrationfiltered
  2. customEvaporation of the mother liquid

Sources & evidence

ORD record
ord-389bbdc05b554c00b14997a842f7992e
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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