2-(Trifluoromethyl)aniline → HCID 68973195, compound

HRID 749049Notes

Reaction equation

HRID 749049 reaction equation
CN1CCOCC1.[F:8][C:9]([F:18])([F:17])[C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12].[O:19]=[C:20]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C:22]([CH2:23][CH2:24][C@@H:25]3[C@@H:34]2[CH2:33][CH2:32][C@@:30]2([CH3:31])[C@H:26]3[CH2:27][CH2:28][C@@H:29]2[C:39](Cl)=[O:40])=[CH:21]1>C(Cl)Cl>[O:19]=[C:20]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C:22]([CH2:23][CH2:24][C@@H:25]3[C@@H:34]2[CH2:33][CH2:32][C@@:30]2([CH3:31])[C@H:26]3[CH2:27][CH2:28][C@@H:29]2[C:39]([NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]([F:17])([F:18])[F:8])=[O:40])=[CH:21]1

Participants

5

Reactant 3

HCID 69222-(Trifluoromethyl)anilineHCID 79724-MethylmorpholineHCID 117273863-Oxoandrost-4-ene-17beta-carbonyl chloride

Product 1

HCID 68973195HCID 68973195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-methylmorpholine (0.28 g, 2.8 mmol) and 2-(trifluoromethyl)aniline (0.5 g, 3.1 mmol) in anhydrous CH2Cl2 (3.0 mL) at 0° C. under a nitrogen atmosphere was added a solution of 3-oxoandrost-4-ene-17β-carbonyl chloride from Step A (2.56 mmol) in anhydrous CH2Cl2 (8.1 mL) dropwise. The ice bath was removed and the mixture stirred at room temperature overnight. The reaction was then concentrated and the residue was purified by flash chromatography on silica gel eluting with 0 to 50% EtOAc-hexanes to afford the desired product as a white solid.

Workup

  1. customThe ice bath was removed
  2. concentrationThe reaction was then concentrated
  3. customthe residue was purified by flash chromatography on silica gel eluting with 0 to 50% EtOAc-hexanes

Sources & evidence

ORD record
ord-ac4f7277ab204c88874899af40acec3c
Source dataset
uspto-grants-2008_07
Patent number
US07402577B2

Reaction notes

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