HCID 89438437, compound → HCID 54675675, compound

HRID 2203328Notes

Reaction equation

HRID 2203328 reaction equation
[NH2:1][C:2]1[C:3]2[C:30]([CH3:37])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:29](=[O:38])[NH:28][C:4]=2[N:5]=[C:6]([NH:8]/[N:9]=[C:10](/[C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=2Br)\[CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[N:7]=1>[Cu]I.CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:30]([CH3:37])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:29](=[O:38])[NH:28][C:4]=2[N:5]=[C:6]([N:8]2[C:21]3[C:20](=[CH:25][C:24]([Cl:26])=[CH:23][CH:22]=3)[C:10]([CH2:11][CH2:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[N:9]2)[N:7]=1

Participants

4

Reactant 1

HCID 89438437HCID 89438437, compound

Product 1

HCID 54675675HCID 54675675, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent2×

Procedure

A DMF (2 mL) solution of the crude intermediate from Step D (73 mg, 0.12 mmol), copper (I) iodide (23 mg, 0.12 mmol) and N,N′-dimethylaminocyclohexane (17 mg, 0.12 mmol) was stirred at room temperature for 30 minutes. The DMF reaction mixture was filtered and purified by reverse phase HPLC using a water/acetonitrile (with 0.1% TFA) gradient to give the indicated compound. 1H NMR (500 MHz, CH3CN-d3): δ 9.17 (s, 1H); 8.83-8.78 (m, 1H); 7.84 (d, T=3.7 Hz, 1H); 7.54-7.49 (m, 1H); 7.38-7.28 (m, 5H); 5.38 (s, 2H); 3.31-3.26 (m, 2H); 2.73-2.66 (m, 2H); 1.82 (s, 3H). m/z=537.2 (M+H).

Workup

  1. filtrationwas filtered
  2. custompurified by reverse phase HPLC
  3. customto give the indicated compound

Sources & evidence

ORD record
ord-2fa72be052354803b2301a55373064cd
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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