1,2-Dichloroethane → HCID 68060115, compound

HRID 2204738Notes

Reaction equation

HRID 2204738 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[C:18]([C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[C:17]([CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:16][C:11]=2[C:12](OC)=[O:13])=[CH:4][CH:3]=1.[OH-].[Li+].Cl.C(N(C(C)C)CC)(C)C.[N:45]1[CH:50]=[CH:49][C:48]([NH2:51])=[CH:47][N:46]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:19]=[C:18]([C:20]3[CH:21]=[N:22][N:23]([CH3:25])[CH:24]=3)[C:17]([CH2:26][N:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)=[CH:16][C:11]=2[C:12]([NH:51][C:48]2[CH:49]=[CH:50][N:45]=[N:46][CH:47]=2)=[O:13])=[CH:6][CH:7]=1

Participants

10

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 2984924-AminopyridazineHCID 66611435HCID 66611435, compound

Product 1

HCID 68060115HCID 68060115, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-{[(4-fluorophenyl)methyl]oxy}-4-(1-methyl-1H-pyrazol-4-yl)-5-(4-morpholinylmethyl)benzoate (may be prepared as described in Description 18; 144 mg, 0.33 mmol) in tetrahydrofuran (4 ml) was added lithium hydroxide (23.54 mg, 0.98 mmol) and water (1 ml). The mixture was stirred at room temperature for 18 hours then neutralised with 2M hydrochloric acid (0.79 ml, 1.59 mmol). The solvent was removed in vacuo and the residue redissolved in N,N-dimethylformamide (4 ml). Diisopropylethylamine (0.11 m, 0.66 mmol), 4-pyridazinamine (40.5 mg, 0.43 mmol), 1-hydroxy-7-azabenzotriazole (53.5 mg, 0.39 mmol) and EDC (94 mg, 0.49 mmol) were added and the solution was stirred for 3 hours. The solvent was removed in vacuo and the residue purified by MDAP to yield the title compound as a white solid. 57 mg.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in N,N-dimethylformamide (4 ml)
  3. stirringthe solution was stirred for 3 hours
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by MDAP

Sources & evidence

ORD record
ord-5723953a1f144313b081368fe68739ac
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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