Aniline → HCID 68621190, compound

HRID 1182482Notes

Reaction equation

HRID 1182482 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C:7]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[O:8])=[CH:3][CH:2]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.[N:38]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2N=N1.NC1C=CC=CC=1>ClCCl>[C:42]1([NH:38][C:15](=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:7]([C:4]2[CH:5]=[CH:6][C:1]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:2][CH:3]=2)=[O:8])[CH:43]=[CH:44][CH:45]=[CH:46][CH:41]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471Triethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 109689257-(4-Biphenyl)carbonylheptanoic acid

Product 1

HCID 68621190HCID 68621190, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of carboxylic acid 50h (310 mg, 1 mmol) in dichloromethane (5 mL) stirred at room temperature under nitrogen was added triethylamine (135 μL, 1 mmol), followed by BOP (442 mg, 1 mmol), aniline (108 μL, 1 mmol) and triethylamine (405 μL, 3 mmol). The resulting reaction mixture was stirred for 12 hours at room temperature. The solvent was removed and the mixture was quenched with water (5 mL), extracted with ethyl acetate (3×10 mL), dried (MgSO4), concentrated. Purification by flash silica gel chromatography (5% methanol in dichloromethane) followed by crystallization from acetone afforded the corresponding amide 80 (20% yield). 1H NMR: (300 MHz, CDCl3) δ 8.00 (m, 4H), 7.40-7.60 (m, 10H), 3.00 (m, 2H), 2.60 (m, 2H), 1.60 (m, 4H), 1.20 (m, 4H).

Workup

  1. customThe resulting reaction mixture
  2. customThe solvent was removed
  3. customthe mixture was quenched with water (5 mL)
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by flash silica gel chromatography (5% methanol in dichloromethane)
  8. customfollowed by crystallization from acetone

Sources & evidence

ORD record
ord-ac9686c0aba14e8bb2c2498b1bf24c5e
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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