Methanesulfonyl chloride → HCID 67083805, compound

HRID 2239507Notes

Reaction equation

HRID 2239507 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:26][CH3:27])=[C:17]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:18]=2)[N:13]=[N:12][C:11]=1[C:28]([NH2:30])=[O:29].C(N(C(C)C)C(C)C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:26][CH3:27])=[C:17]([CH:20]3[CH2:25][CH2:24][N:23]([S:41]([CH3:40])(=[O:43])=[O:42])[CH2:22][CH2:21]3)[CH:18]=2)[N:13]=[N:12][C:11]=1[C:28]([NH2:30])=[O:29]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67083714HCID 67083714, compound

Product 1

HCID 67083805HCID 67083805, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(2-fluoro-4-methylphenylamino)-7-methoxy-6-(piperidin-4-yl)cinnoline-3-carboxamide (Example 51, 0.1 g, 0.24 mmol) in CH2Cl2 (2.5 ml) and DMF (2.5 ml) was added N-ethyldiisopropylamine (0.127 ml, 0.73 mmol) and methanesulphonyl chloride (0.021 ml, 0.27 mmol). The reaction mixture was stirred at for 1 hour, diluted with CH2Cl2 and washed with water. The organic layer was concentrated under reduced pressure and the residue purified by reverse phase chromatography using 0.1% formic acid in water and methanol (50-70%) to give 28 mg (24%) off-white solid. 1H NMR: 11.56 (s, 1H), 8.78 (s, 1H), 7.94 (s, 1H), 7.61 (s, 1H), 7.29 (m, 1H), 7.21 (m, 1H), 7.11 (m, 2H), 4.01 (s, 3H), 3.51 (m, 2H), 2.91 (m, 1H), 2.84 (s, 3H), 2.74 (m, 2H), 2.35 (s, 3H), 1.63 (m, 2H), 0.97 (m, 2H); m/z 488.

Workup

  1. washwashed with water
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue purified by reverse phase chromatography

Sources & evidence

ORD record
ord-1b05ae337d2642c194bd6ef97ab98e9d
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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