Hydrazine hydrate (1:1) → HCID 178420869, compound

HRID 273065Notes

Reaction equation

HRID 273065 reaction equation
C[N:2]([CH:4]=[N:5][C:6]([C:8]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][CH:15]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=O)C.O.[NH2:30]N>C(O)(=O)C>[N:24]1([CH2:23][CH2:22][CH2:21][O:20][C:17]2[CH:18]=[CH:19][C:14]([C:8]3([C:6]4[N:5]=[CH:4][NH:2][N:30]=4)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:15][CH:16]=2)[CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68578480HCID 68578480, compound

Product 1

HCID 178420869HCID 178420869, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

N-[(dimethylamino)methylene]-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carboxamide (0.15 g, 0.39 mmol), hydrazine hydrate (0.048 mL, 0.98 mmol) and acetic acid (1 mL) were combined and heated at 100° C. for 1.5 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL) and washed with 10% aqueous sodium carbonate (20 mL). The organic was dried over sodium sulphate and evaporated to provide a clear oil. This was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (92:8:0.8 to 90:10:1) to produce a clear oil which was triturated with diethyl ether (3 mL), a white solid was isolated as the title compound (0.034 g, 24%). 1H NMR (400 MHz, CDCl3) δ 1.82-1.95 (m, 4H), 2.0-2.10 (m, 2H), 2.30 (m, 2H), 2.60-2.70 (m, 2H), 2.70-2.80 (m, 6H), 3.62 (t, 2H), 3.89 (m, 2H), 3.95 (t, 2H), 6.80 (d, 2H), 7.20 (d, 2H), 7.95 (d, 1H). HRMS ESI+ m/z 357.2279 [MH]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  3. washwashed with 10% aqueous sodium carbonate (20 mL)
  4. dry with materialThe organic was dried over sodium sulphate
  5. customevaporated
  6. customto provide a clear oil
  7. customThis was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (92:8:0.8 to 90:10:1)
  8. customto produce a clear oil which
  9. customwas triturated with diethyl ether (3 mL)

Sources & evidence

ORD record
ord-953fb39b7e244f0295e5ea21e76e7a58
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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