Ammonium formate → HCID 71268444, compound

HRID 529120Notes

Reaction equation

HRID 529120 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:17][CH2:16][C:15]2([C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[N:19]([C:35]3[C:36]4[C@H:43]([CH3:44])[CH2:42][CH2:41][C:37]=4[N:38]=[CH:39][N:40]=3)[CH2:18]2)[CH2:14][CH2:13]1)C1C=CC=CC=1>CO.[Pd]>[CH3:44][C@H:43]1[C:36]2[C:35]([N:19]3[C:20]4[C:25](=[C:24]([CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH:23]=[CH:22][CH:21]=4)[C:15]4([CH2:14][CH2:13][NH:12][CH2:17][CH2:16]4)[CH2:18]3)=[N:40][CH:39]=[N:38][C:37]=2[CH2:41][CH2:42]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86651808HCID 86651808, compound

Product 1

HCID 71268444HCID 71268444, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (1.82 g, 28.9 mmol) and 10% Pd/C (0.31 g, 20% weight) was added to a solution of (R)-tert-butyl (1′-benzyl-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methylcarbamate (1.56 g, 2.89 mmol) in MeOH (28 mL). The mixture was allowed to stir at reflux for 4 hours. After cooling, the reaction mixture was filtered through Celite. The filtrate was evaporated in vacuo. The crude product was taken up in DCM, washed with saturated aqueous NaHCO3 solution and brine, dried and concentrated. The residue was purified by column chromatography (5% 7N ammonia in MeOH/DCM) to give (R)-tert-butyl (1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methylcarbamate (1.01 g, 78%). LCMS (APCI+) m/z 450 [M+H]+; Rt=2.15 min.

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered through Celite
  4. customThe filtrate was evaporated in vacuo
  5. washwashed with saturated aqueous NaHCO3 solution and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (5% 7N ammonia in MeOH/DCM)

Sources & evidence

ORD record
ord-8bad343a170047ec89900f0ed1f8dc5b
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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