1,2-Dichloroethane → HCID 66611053, compound

HRID 2204770Notes

Reaction equation

HRID 2204770 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:15]([C:25]([F:28])([F:27])[F:26])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:38][C:39]1[CH:40]=[C:41]([CH:43]=[CH:44][CH:45]=1)[NH2:42].ON1C2N=CC=CC=2N=N1.C(Cl)CCl>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:15]([C:25]([F:26])([F:28])[F:27])=[CH:14][C:10]=1[C:11]([NH:42][C:41]1[CH:43]=[CH:44][CH:45]=[C:39]([Cl:38])[CH:40]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79323-ChloroanilineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66611544HCID 66611544, compound

Product 1

HCID 66611053HCID 66611053, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(benzyloxy)-4-(morpholinomethyl)-5-(trifluoromethyl)benzoic acid (may be prepared as described in description 50, 270 mg, 0.683 mmol) in N,N-Dimethylformamide (DMF) (5 mL) was added DIPEA (0.239 mL, 1.366 mmol), 3-chloroaniline (72.0 μl, 0.683 mmol), 1-hydroxy-7-azabenzotriazole (112 mg, 0.819 mmol) and EDC (262 mg, 1.366 mmol). The solution was stirred for 3 hours then partitioned between EtOAc (20 ml) and water (15 ml). The organic layer was separated, washed further with water (2×20 ml), dried (MgSO4) and the solvent removed. Purification by column (SiO2, Isolute, 3:1-1:1 Cyclohexane/EtOAc) gave the product as a white solid. 205 mg.

Workup

  1. customthen partitioned between EtOAc (20 ml) and water (15 ml)
  2. customThe organic layer was separated
  3. washwashed further with water (2×20 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed
  6. customPurification by column (SiO2, Isolute, 3:1-1:1 Cyclohexane/EtOAc)

Sources & evidence

ORD record
ord-b736a0c6d4c149f4b60d9c4e1450c1c1
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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