1,2-Dichloroethane → HCID 68108731, compound

HRID 1623873Notes

Reaction equation

HRID 1623873 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]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.[NH2:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>O1CCCC1.CN(C)C=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:16][C:11]=2[C:12]([NH:41][C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)=[O:14])=[CH:4][CH:3]=1

Participants

11

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 67107724HCID 67107724, compound

Product 1

HCID 68108731HCID 68108731, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[3-(4-morpholinyl)propyl]benzoate (may be prepared as described in Description 124; 166 mg, 0.43 mmol) in tetrahydrofuran (6 ml) was added lithium hydroxide (61.6 mg, 2.57 mmol) and water (1.5 ml). The mixture was stirred at 50° C. for 3 hours, cooled and the acidified with 2M hydrochloric acid (1.29 ml, 2.57 mmol). The solvent was removed in vacuo to give a residue. The residue was redissolved in N,N-dimethylformamide (3 ml) and diisopropylethylamine (0.15 ml, 0.86 mmol), 3-aminopyridine (52.4 mg, 0.56 mmol), 1-hydroxy-7-azabenzotriazole (70.0 mg, 0.51 mmol) and EDC (140 mg, 0.73 mmol). The solution was stirred overnight, the solvent removed in vacuo and the residue was purified by MDAP to yield the title compound as a white solid. 25 mg.

Workup

  1. temperaturecooled
  2. customThe solvent was removed in vacuo
  3. customto give a residue
  4. stirringThe solution was stirred overnight
  5. customthe solvent removed in vacuo
  6. customthe residue was purified by MDAP

Sources & evidence

ORD record
ord-8c3e1c46df2d4f3c8b8bb32d512afc89
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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