Potassium Carbonate → HCID 59451896, compound

HRID 1971249Notes

Reaction equation

HRID 1971249 reaction equation
[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([CH2:24]Cl)[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH:26]1[CH2:30][CH2:29][C@@H:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O.O>[C:34]([O:33][C:32](=[O:38])[NH:31][C@@H:28]1[CH2:29][CH2:30][N:26]([CH2:24][C:22]2[N:23]=[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([C:13](=[O:14])[NH:12][CH2:11][C:1]45[CH2:10][CH:5]6[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]6)[CH2:2]4)[CH2:8]5)[N:20]3[CH:21]=2)[CH2:27]1)([CH3:37])([CH3:35])[CH3:36]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 59451927HCID 59451927, compound

Product 1

HCID 59451896HCID 59451896, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-(adamantanylmethyl)-2-(chloromethyl)imidazo[1,2-a]pyridine-5-carboxamide (HCl salt, 700 mg, 1.78 mmol), tert-butyl (3R)-pyrrolidin-3-ylcarbamate (496 mmol, 2.66 mmol) and potassium carbonate (615 mg, 4.45 mmol) in DMF (25 mL) is stirred at RT for 20 h. The reaction mixture is diluted with EtOAc and water. The organic layer is separated, and the aqueous layer is back extracted with EtOAc. The combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. Purification of the residue by silica gel chromatography (10% MeOH, 1% NH4OH in DCM) affords the title compound. 1H-NMR (δ, ppm, CDCl3 as internal standard): 8.35 (s, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.15 (dd, J=7.2 and 9.0 Hz, 1H), 7.08 (d, J=6.9 Hz, 1H), 6.33 (t, J=5.7 Hz, 1H), 4.16 (m, 1H), 3.85 (d, J=13.5 Hz, 1H), 3.78 (d, J=13.2 Hz, 1H), 3.2 (d, J=6.6 Hz, 2H), 2.91-2.64 (m, 2H), 2.44-2.21 (m, 2H), 2.02 (m, 3H), 1.77-1.58 (m, 15H), 1.41 (s, 9H).

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is back extracted with EtOAc
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the residue by silica gel chromatography (10% MeOH, 1% NH4OH in DCM)

Sources & evidence

ORD record
ord-1b8fa3e3309841e29f8e0a7824d959fd
Source dataset
uspto-grants-2013_04
Patent number
US08431593B2

Reaction notes

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