Dimethylformamide → HCID 86688144, compound

HRID 1622565Notes

Reaction equation

HRID 1622565 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:12]([C:14]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=2)[NH2:13])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].CCN(C(C)C)C(C)C.[N:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.CN([CH:45]=[O:46])C>C(Cl)Cl>[F:9][C:8]([F:11])([F:10])[C:45]([OH:46])=[O:36].[F:1][C:2]1[CH:3]=[C:4]([C@@H:12]([C:14]2[C:19]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:17]=[CH:16][N:15]=2)[NH:13][C:39]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:40])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 86687952HCID 86687952, compound2×

Product 1

HCID 86688144HCID 86688144, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(3-fluoro-4-(trifluoromethyl)phenyl)(3-(trifluoro-methyl)pyridin-2-yl)methanamine (Intermediate 7) (100 mg, 0.296 mmol) and DIPEA (0.101 mL, 0.591 mmol) in DCM (1.0 mL) was added morpholine-4-carbonyl chloride (66.3 mg, 0.443 mmol). The resulting reaction mixture was stirred at rt for 19 h. The reaction was then diluted with DMF (2 mL), filtered through a syringe filter, and purified by reverse phase HPLC (Phenomenx Gemini Axia™-5μ C-18 column (150×30 mm) 10-100% MeCN/0.1% TFA in H2O ). The product-containing fractions were combined, and the solvent was removed by lyophilization to give the title compound as a white solid. 1H NMR (300 MHz, d4-MeOH) δ ppm 8.66-8.43 (m, 1H), 7.84 (d, J=7.9 Hz, 1H), 7.38-7.12 (m, 2H), 7.07-6.83 (m, 2H), 6.26 (s, 1H), 3.35 (peak obscured by solvent), 3.08 (br. s., 4H), 2.98 (br. s., 2H). MS (ESI pos. ion) m/z: 452.0 (M+H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered through a syringe
  3. filtrationfilter
  4. custompurified by reverse phase HPLC (Phenomenx Gemini Axia™-5μ C-18 column (150×30 mm) 10-100% MeCN/0.1% TFA in H2O )
  5. customthe solvent was removed by lyophilization

Sources & evidence

ORD record
ord-c5f3ce7df60d4186ae931b16fbed9c52
Source dataset
uspto-grants-2014_07
Patent number
US08778941B2

Reaction notes

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