Hydrazinecarboxaldehyde → N'-formyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbohydrazide

HRID 273067Notes

Reaction equation

HRID 273067 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22](O)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:25]([NH:27][NH2:28])=[O:26].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl>[CH:25]([NH:27][NH:28][C:22]([C:16]1([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:15][CH:14]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:23])=[O:26]

Participants

7

Reactant 5

HCID 12229HydrazinecarboxaldehydeHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 598374194-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carboxylic acid

Product 1

HCID 68576159N'-formyl-4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbohydrazideYield 171.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carboxylic acid (0.75 g, 0.225 mmol), formic hydrazide (0.162 g, 0.27 mmol), 1-hydroxybenzotriazole (0.304 g, 0.225 mmol), diisopropylethylamine (1.18 mL, 0.68 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.431 g, 0.225 mmol) in dichloromethane (10 mL) was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (100 mL) and washed with water (2×20 mL) The organics were dried over sodium sulphate, filtered and concentrated in vacuo to provide a cream solid. This was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 to 90:10:1) to provide the title compound (0.145 g, 17%) as a clear oil. LRMS ESI+ m/z 376 [MH]+, ESI− m/z 374 [M−H+]−.

Workup

  1. washwashed with water (2×20 mL) The
  2. dry with materialorganics were dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a cream solid
  6. customThis was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (95:5:0.5 to 90:10:1)

Sources & evidence

ORD record
ord-b0c58b14e0fe4695a91cfdbbc34e085b
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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