Water → HCID 66779661, compound

HRID 1470388Notes

Reaction equation

HRID 1470388 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[C:20]3[C:21]([CH3:27])=[C:22]([CH:24]=[CH:25][CH:26]=3)[NH2:23])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[F:35][C:36]([F:47])([F:46])[C:37]1[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=1)[C:40](Cl)=[O:41].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[C:20]3[C:21]([CH3:27])=[C:22]([NH:23][C:40](=[O:41])[C:39]4[CH:43]=[CH:44][CH:45]=[C:37]([C:36]([F:35])([F:46])[F:47])[CH:38]=4)[CH:24]=[CH:25][CH:26]=3)[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 66779773HCID 66779773, compound

Product 1

HCID 66779661HCID 66779661, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20-mL glass vial was added 3-[2-(3,4-dimethoxyphenyl)furo[3,2-b]pyridin-7-yl]-2-methylaniline (19.20 mg; 0.05 mmol), triethylamine (0.01 ml; 0.11 mmol) suspended in DCM (2.00 ml). 3-(trifluoromethyl)benzoyl chloride (16.67 mg; 0.08 mmol) was then added. The reaction mixture was stirred at room temperature overnight. Water was added to the reaction mixture which was then extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude mixture was purified using Biotage column chromatography (20-100% EtOAc/Hexanes). Fractions containing the desired product were combined and concentrated. The mixture was then purified using preparative HPLC to afford the title compound as a yellow solid (3.80 mg, 13%). HPLC (method F): 100%, RT=4.531 min. 1H NMR (CDCl3) δ [ppm] 8.58 (d, 1H), 8.19 (s, 1H), 8.12 (d, 1H), 7.96 (d, 1H), 7.88-7.84 (m, 2H), 7.71-7.68 (m, 2H), 7.60-7.47 (m, 3H), 7.39-7.38 (m, 2H), 7.00-6.97 (m, 1H), 4.01 (s, 3H), 3.96 (s, 3H), 2.27 (s, 3H). MS: m/z=533 [M+H]+, RT=3.91 min.

Workup

  1. extractionwas then extracted with EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude mixture was purified
  6. additionFractions containing the desired product
  7. concentrationconcentrated
  8. customThe mixture was then purified

Sources & evidence

ORD record
ord-9fe2c804dcff462d936e100a6a8fc0de
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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