Aniline → HCID 9982385, compound

HRID 1768483Notes

Reaction equation

HRID 1768483 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH2:25][CH2:26][C:27]([OH:29])=O)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1.[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[NH:30]([C:27](=[O:29])[CH2:26][CH2:25][C:11]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=[C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[CH2:13][N:12]1[C:14]([N:16]([CH3:17])[CH3:18])=[O:15])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 10046528HCID 10046528, compound

Product 1

HCID 9982385HCID 9982385, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 40 mg (0.10 mmol) of acid 24-1 in DMF was added 11 μL (0.12 mmol) of aniline, 29 mg (0.15 mmol) of EDCI, 17 mg (0.13 mmol) HOAT, and 28 μL (0.20 mmol) of triethylamine. After stirring overnight at room temperature, the reaction was partitioned between EtOAc and 10% KHSO4, the organic phase was washed with saturated NaHCO3, brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography on silica gel with EtOAc/hexanes to provide 24-2 as a white solid. Data for 24-2: 1HNMR (500 MHz, d6-DMSO) δ 9.8 (s, 1H), 7.5-7.0 (m, 13H), 6.2 (s, 1H), 5.0 (m, 1H), 4.8 (m, 1H), 3.0 (m, 1H), 2.75 (s, 6H), [(˜2.5, under solvent peak (m, 1H)], 2.2 (m, 2H) ppm. HRMS (ES) calc'd M+H for C28H27F2N3O2: 476.2144. Found: 476.2162

Workup

  1. customthe reaction was partitioned between EtOAc and 10% KHSO4
  2. washthe organic phase was washed with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel with EtOAc/hexanes

Sources & evidence

ORD record
ord-3a1beb2ac1db4ad5b88e82e9d36ae207
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

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