Dimethylformamide → HCID 58046633, compound

HRID 1750977Notes

Reaction equation

HRID 1750977 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1)=[O:4].O=C1[C:17]2([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[N:16]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)CN1.[C:36](=[O:39])([O-:38])[O-].[K+].[K+].[CH3:42][N:43]([CH3:46])[CH:44]=[O:45]>C(OCC)(=O)C>[CH3:11][N:8]1[CH2:9][CH2:10][N:5]([C:3](=[O:4])[CH2:2][O:38][C:36]([C:30]2[CH:31]=[C:32]([CH:33]=[CH:34][CH:35]=2)[CH2:42][N:43]2[C:44](=[O:45])[C:17]3([CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[N:16]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH2:46]2)=[O:39])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 389488tert-Butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylateHCID 8181732-Chloro-1-(4-methylpiperazin-1-yl)ethanone

Product 1

HCID 58046633HCID 58046633, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 2-chloro-1-(4-methylpiperazin-1-yl)ethanone in N,N-dimethylformamide (3 mL), was added tert-butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate (0.2 g, 0.43 mmol) and potassium carbonate (0.119 g, 0.86 mmol). After stirring at 65° C. for 18 hours, the reaction mixture was diluted with ethyl acetate (25 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgSO4, filtered and isolated by Biotage flash chromatography (2-20% methanol/dichloromethane) to obtain the title compound (0.16 g, 62%); 1H NMR (DMSO-d6): δ 1.45 (s, 9H), 1.64 (t, 2H, J=12.8 Hz), 2.18 (s, 3H), 2.25-2.45 (m, 6H), 3.41-3.50 (m, 6H), 3.85 (br, 2H), 4.60-4.65 (m, 4H), 5.05 (s, 2H), 6.64-6.69 (m, 2H), 6.76-6.79 (m, 1H), 7.13-7.19 (m, 2H), 7.54-7.60 (m, 2H), 7.91-7.93 (m, 2H); MS for C33H43N5O6 m/z 606.08 (M+H)+.

Workup

  1. washwashed with dilute citric acid, water and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customisolated by Biotage flash chromatography (2-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-685baf2421474fc6a8c3e01ee05bb8ac
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

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