Methanesulfonyl chloride → HCID 68703936, compound

HRID 889312Notes

Reaction equation

HRID 889312 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11]2[C:15](=[O:16])[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][NH:12]2)[CH:6]=1.[CH3:23][S:24]([Cl:27])(=[O:26])=[O:25].C(N(CC)C(C)C)(C)C>CN(C=O)C>[ClH:27].[O:16]=[C:15]1[N:11]([C:7]2[CH:6]=[C:5]([CH2:4][NH:3][S:24]([CH3:23])(=[O:26])=[O:25])[CH:10]=[CH:9][N:8]=2)[NH:12][CH:13]=[C:14]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 68704213HCID 68704213, compound

Product 1

HCID 68703936HCID 68703936, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80.0 mg (235 μmol) of the compound from Example 35 and 53.9 mg (470 μmol) methanesulfonic acid chloride are dissolved in 5 ml DMF under argon and while cooling with ice, 152 mg (1.18 mmol) N,N-diisopropylethylamine are added and the mixture is stirred overnight at RT. The reaction mixture is then purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% conc. hydrochloric acid).

Workup

  1. additionare added
  2. customThe reaction mixture is then purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% conc. hydrochloric acid)

Sources & evidence

ORD record
ord-48cb9050a8394d2886ef002557e48ffb
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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