1,2-Dichloroethane → HCID 66635623, compound

HRID 2204758Notes

Reaction equation

HRID 2204758 reaction equation
[N:1]1([C:7]([C:9]2[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][C:12]([C:13](OCC3C=CC=CC=3)=[O:14])=[C:11]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Li+].Cl.C(N(C(C)C)CC)(C)C.[NH2:49][C:50]1[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=1.ON1C2N=CC=CC=2N=N1.C(Cl)CCl>O1CCCC1.O.C(OCC)(=O)C>[N:1]1([C:7]([C:9]2[C:24]([C:25]([F:27])([F:26])[F:28])=[CH:23][C:12]([C:13]([NH:49][C:50]3[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=3)=[O:14])=[C:11]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:10]=2)=[O:8])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

11

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 100093-AminopyridineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66611389HCID 66611389, compound

Product 1

HCID 66635623HCID 66635623, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of phenylmethyl 4-(4-morpholinylcarbonyl)-2-[(phenylmethyl)oxy]-5-(trifluoromethyl)benzoate (may be prepared as described in Description 56; 64 mg, 0.13 mmol) in tetrahydrofuran (3 ml) was added lithium hydroxide (9.21 mg, 0.38 mmol) and water (0.75 ml). The solution was heated at 45° C. for one hour, cooled and 2M hydrochloric acid (0.19 ml, 0.38 mmol) was added. The solvent was removed in vacuo and the residue redissolved in N,N-dimethylformamide (4 ml). Diisopropylethylamine (0.06 ml, 0.32 mmol), 3-aminopyridine (18.09 mg, 0.19 mmol), 1-hydroxy-7-azabenzotriazole (22.67 mg, 0.17 mmol) and EDC (44.2 mg, 0.23 mmol) were added and the mixture was stirred for 18 hours. Ethyl acetate (20 ml) and water (10 ml) were added and the organic layer washed further with water (2×5 ml), dried (MgSO4) and the solvent removed in vacuo to give a gum. Purification by MDAP gave the title compound as a white solid. 38 mg.

Workup

  1. temperaturecooled
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue redissolved in N,N-dimethylformamide (4 ml)
  4. washthe organic layer washed further with water (2×5 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customto give a gum
  8. customPurification by MDAP

Sources & evidence

ORD record
ord-80477f00ae154c74bce709896f9b264e
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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