HCID 1476965, compound → HCID 57833087, compound

HRID 729640Notes

Reaction equation

HRID 729640 reaction equation
CN([CH:4]=[C:5]1[C:10](=O)[CH2:9][CH2:8][N:7]([CH3:12])[CH2:6]1)C.Cl.[NH2:14][C:15](=[NH:29])[N:16]1[CH2:20][CH2:19][C@@H:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17]1.C[O-].[Na+]>CO>[C:24]([O:23][C:22](=[O:28])[NH:21][C@@H:18]1[CH2:19][CH2:20][N:16]([C:15]2[N:14]=[CH:4][C:5]3[CH2:6][N:7]([CH3:12])[CH2:8][CH2:9][C:10]=3[N:29]=2)[CH2:17]1)([CH3:26])([CH3:25])[CH3:27]

Participants

5

Reactant 3

HCID 1476965HCID 1476965, compoundHCID 10942334Sodium MethoxideHCID 86622701HCID 86622701, compound

Product 1

HCID 57833087HCID 57833087, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-[(Dimethylamino)methylene]-1-methylpiperidin-4-one (9.04 g, 53.7 mmol) and tert-butyl {(3R)-1-[amino(imino)methyl]pyrrolidin-3-yl}carbamate hydrochloride (14.2 g, 53.7 mmol) were dissolved in methanol (100 mL) and to this was added dropwise sodium methoxide (9.66 g of a 30% solution in methanol). The reaction mixture was refluxed for 3 hours and then cooled to room temperature. The reaction mixture was then evaporated to dryness, and the residue was treated with water (50 mL). The precipitate was separated by filtration, washed with water (25 mL) and diethyl ether (50 mL) and dried to give the title compound 10.43 g (yield 58%). LCMS (ES+) M+H 334. 1H NMR (DMSO-d6) 1.39 (s, 9H) 1.85 (m, 1H) 2.13 (m, 1H) 2.33 (s, 3H) 2.60 (m, 2H) 2.67 (m, 2H) 3.23-3.26 (m, 1H) 3.31-3.37 (m, 3H) 3.40-3.536 (m, 1H) 3.63 (m, 1H) 4.04 (br s, 1H) 7.20 (br s, 1H) 8.04 (s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customThe reaction mixture was then evaporated to dryness
  3. additionthe residue was treated with water (50 mL)
  4. customThe precipitate was separated by filtration
  5. washwashed with water (25 mL) and diethyl ether (50 mL)
  6. customdried

Sources & evidence

ORD record
ord-a379dd958560455bb00541f01fa20352
Source dataset
uspto-grants-2009_09
Patent number
US07582643B2

Reaction notes

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