Aminoacetaldehyde dimethyl acetal → HCID 58497247, compound

HRID 467507Notes

Reaction equation

HRID 467507 reaction equation
Cl.CN(C)CCCN=C=NCC.[F:13][C:14]1[CH:15]=[C:16]([C:21]2[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH2:28][C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=3)[C:32](O)=[O:33])[N:22]=2)[CH:17]=[C:18]([F:20])[CH:19]=1.[CH3:38][O:39][CH:40]([O:43][CH3:44])[CH2:41][NH2:42].O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O>[F:13][C:14]1[CH:15]=[C:16]([C:21]2[CH:26]=[CH:25][C:24](=[O:27])[N:23]([CH2:28][C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=3)[C:32]([NH:42][CH2:41][CH:40]([O:43][CH3:44])[O:39][CH3:38])=[O:33])[N:22]=2)[CH:17]=[C:18]([F:20])[CH:19]=1

Participants

7

Reactant 4

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59534515HCID 59534515, compound

Product 1

HCID 58497247HCID 58497247, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

906 mg (4.73 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI) are added to a solution of 1.24 g (3.64 mmol) of 3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]benzoic acid (prepared in accordance with WO 2008/017361), 382 mg (3.64 mmol) of aminoacetaldehyde dimethyl acetal and 557 mg (3.64 mmol) of 1-hydroxybenzotriazole hydrate (HOBt) in 14 ml of DMF, and the mixture is stirred overnight at room temperature. Water is added to the reaction mixture. The precipitate formed is filtered off with suction, washed with water and dried in vacuo, giving 3-[3-(3,5-difluorophenyl)-6-oxo-6H-pyridazin-1-ylmethyl]-N-(2,2-dimethoxyethyl)benzamide as colourless crystals; ESI 430.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off with suction
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e3e1b89240184e01909610caff05b0da
Source dataset
uspto-grants-2014_01
Patent number
US08623870B2

Reaction notes

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