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1,2-Dichloroethane → 3-Chloro-6-methyl-pyridazine-4-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

HRID 1486750
Notes
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Reaction equation

HRID 1486750 reaction equation
[C:1]([NH:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[N:24]=[N:25][C:26]([CH3:32])=[CH:27][C:28]=1[C:29](O)=[O:30].C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([NH:5][C:6]([CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([NH:21][C:29]([C:28]3[CH:27]=[C:26]([CH3:32])[N:25]=[N:24][C:23]=3[Cl:22])=[O:30])[CH:18]=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 265992153-Chloro-6-methylpyridazine-4-carboxylic acidHCID 867065251-(3-Amino-benzyl)-piperidine-4-carboxylic acid tert-butylamide

Product 1

HCID 1185218653-Chloro-6-methyl-pyridazine-4-carboxylic acid [3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-amino-benzyl)-piperidine-4-carboxylic acid tert-butylamide BB-4 (400 mg, 1.4 mmol) in DCM (15 mL) is treated successively with 3-chloro-6-methyl-pyridazine-4-carboxylic acid (239 mg, 1.4 mmol), EDC (344 mg, 1.8 mmol) and DMAP (25.3 mg, 0.207 mmol) at RT overnight. The reaction mixture is washed twice with sat.aq. NaHCO3 (15 mL). The aqueous phase is extracted twice with DCM (2×10 mL). The combined organic layers are dried over MgSO4 and filtered. The solvent is evaporated under reduced pressure. The residue is purified by prep HPLC E delivering the title compound (53 mg, 36%) as a light brownish powder, LC-MS A: tR=0.60 min; [M+H]+=444.12.

Workup

  1. washThe reaction mixture is washed twice with sat.aq
  2. extractionThe aqueous phase is extracted twice with DCM (2×10 mL)
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent is evaporated under reduced pressure
  6. customThe residue is purified by prep HPLC E

Sources & evidence

ORD record
ord-7954e4882bd14dbc9cc23f7fd0fa971a
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428456B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes