Ammonium formate → HCID 68736214, compound

HRID 529156Notes

Reaction equation

HRID 529156 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[CH2:22][N:23]([CH:31]([CH3:33])[CH3:32])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[N:15]([C:34]3[C:35]4[CH:42]([CH:43]([CH3:45])[CH3:44])[CH2:41][CH2:40][C:36]=4[N:37]=[CH:38][N:39]=3)[CH2:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH:31]([N:23]([CH2:22][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[N:15]([C:34]3[C:35]4[CH:42]([CH:43]([CH3:45])[CH3:44])[CH2:41][CH2:40][C:36]=4[N:37]=[CH:38][N:39]=3)[CH2:14][C:11]3([CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:21]=12)[C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:29])[CH3:27])([CH3:33])[CH3:32]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86651817HCID 86651817, compound

Product 1

HCID 68736214HCID 68736214, compoundYield 783.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of tert-butyl (1′-benzyl-1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl(isopropyl)carbamate (0.088 g, 0.14 mmol) in MeOH (1 mL) was treated with ammonium formate (0.027 g, 0.43 mmol) and Pd/C (0.0077 g, 0.0072 mmol) and heated to reflux for 7 hours and stirred at room temperature overnight. The reaction was filtered through glass filter paper, and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography (5% MeOH/DCM, then 5% 7N N1—I4 in MeOH/DCM) to yield pure tert-butyl isopropyl((1-(5-isopropyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)methyl)carbamate (0.57 g, 76%). LCMS (APCI+) m/z 520.2 [M+H]+; Rt=3.80 min.

Workup

  1. temperatureheated
  2. temperatureto reflux for 7 hours
  3. filtrationThe reaction was filtered through glass
  4. filtrationfilter paper
  5. customthe solvent was removed under reduced pressure
  6. customThe crude residue was purified by column chromatography (5% MeOH/DCM

Sources & evidence

ORD record
ord-602df7cadbc1462896d86fee0c29d425
Source dataset
uspto-grants-2016_05
Patent number
US09346805B2

Reaction notes

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