1,2-Dichloroethane → HCID 66614596, compound

HRID 2204737Notes

Reaction equation

HRID 2204737 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]([O:14]C)=O)=[CH:4][CH:3]=1.[OH-].[Li+].Cl.C(N(C(C)C)CC)(C)C.[NH2:45][C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>O1CCCC1.O>[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[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)=[CH:16][C:11]=2[C:12]([NH:45][C:46]2[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=2)=[O:14])=[CH:4][CH:3]=1

Participants

10

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66611435HCID 66611435, compound

Product 1

HCID 66614596HCID 66614596, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

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; 155 mg, 0.353 mmol) in tetrahydrofuran (4 ml) was added lithium hydroxide (31 mg, 1.29 mmol) followed by water (1 ml). The mixture was heated at 50° C. for one hour. 2M hydrochloric acid (0.79 ml, 1.59 mmol) was added and the solvent removed in vacuo. The residue was redissolved in N,N-dimethylformamide (4 ml) and diisopropylethylamine (0.12 ml, 0.71 mmol), 3-aminopyridine (43.2 mg, 0.46 mmol), 1-hydroxy-7-azabenzotriazole (57.6 mg, 0.42 mmol) and EDC (101 mg, 0.53 mmol) were added. The solution was stirred overnight, then the solvent was removed in vacuo to give a residue. Purification by MDAP yielded the title compound as a white solid. 84 mg.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was redissolved in N,N-dimethylformamide (4 ml)
  3. customthe solvent was removed in vacuo
  4. customto give a residue
  5. customPurification by MDAP

Sources & evidence

ORD record
ord-e52e904e44184e59a23de712df4bc4b6
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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