Acetic Acid → HCID 59837534, compound

HRID 273066Notes

Reaction equation

HRID 273066 reaction equation
CN([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.[CH3:29][NH:30][NH2:31].C(O)(=O)C.ClCCl>O.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:29][N:30]1[C:6]([C:8]2([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:25][CH2:26][CH2:27][CH2:28]4)=[CH:16][CH:15]=3)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)=[N:5][CH:4]=[N:31]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 6344DichloromethaneHCID 68578480HCID 68578480, compound

Product 1

HCID 59837534HCID 59837534, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

N-[(dimethylamino)methylene]-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carboxamide (0.34 g, 0.88 mmol), methyl hydrazine (0.116 mL, 2.19 mmol) and acetic acid (1 mL) were combined and heated at 100° C. for 2 hours. The reaction mixture was diluted with water (10 mL), solid sodium carbonate was added until the mixture was pH9. Dichloromethane (2×50 mL) was used to extract. The combined organics were dried over sodium sulphate, filtered and concentrated in vacuo to provide a yellow oil. This was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4 to 90:10:1) to produce the title compound (0.065 g, 20%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.83-1.93 (m, 4H), 2.05-2.16 (m, 2H), 2.30 (m, 2H), 2.48 (m, 2H), 2.60-2.85 (m, 6H), 3.37 (s, 3H), 3.80 (m, 2H), 3.90 (m, 2H), 4.0 (t, 2H), 6.85 (d, 2H), 7.07 (d, 2H), 7.88 (s, 1H). HRMS ESI+ m/z 371.2434 [MH]+.

Workup

  1. additionwas added until the mixture
  2. extractionto extract
  3. dry with materialThe combined organics were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a yellow oil
  7. customThis was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (96:4:0.4 to 90:10:1)

Sources & evidence

ORD record
ord-b79c1b31c56444eca77ac1f332d02715
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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