Methanesulfonic Acid → HCID 11606046, compound

HRID 2425092Notes

Reaction equation

HRID 2425092 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[Cl:6][C:7]1[C:12]2[O:13][C:14]3[C:23]([CH3:24])=[CH:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][C:15]=3[S:16](=[O:19])(=[O:18])[CH2:17][C:11]=2[CH:10]=[C:9]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:8]=1>CO>[S:2]([OH:5])(=[O:4])(=[O:3])[CH3:1].[Cl:6][C:7]1[C:12]2[O:13][C:14]3[C:23]([CH3:24])=[CH:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][C:15]=3[S:16](=[O:18])(=[O:19])[CH2:17][C:11]=2[CH:10]=[C:9]([N:28]2[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]2)[CH:8]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 11606047HCID 11606047, compound

Product 1

HCID 11606046HCID 11606046, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of methane sulfonic acid (0.058 mL, 0.852 mmol) in methanol (1 mL) was added to a solution of compound of Example 18 (0.3 g, 0.710 mmol) in methanol (10 mL) at 25° C. and filtered. The solution was stirred for 1 h and the precipitated solid was filtered, washed using methanol and dried to obtain the title compound. Yield: 0.244 g, (66%); mp 278-280° C.; 1H NMR (DMSO-d6, 300 MHz): δ 2.31 (s, 3H, CH3), 2.62 (s, 3H, CH3), 3.21 (s, 4H, 2CH2), 3.38 (s, 4H, 2CH2), 5.16 (s, 2H, CH2), 7.19 (s, 1H, Ar), 7.19 (s, 1H, Ar), 8.06 (s, 1H, Ar), 8.13 (s, 1H, Ar), 8.80 (s, 1H, NH); MS: m/e (ES+) 423 (M+1, freebase); analysis: C20H23ClN2O8S2 requires C, 46.29; H, 4.47; N, 5.40; Cl, 6.83; S, 12.36. found: C, 46.75; H, 4.26; N, 5.37; Cl, 7.33; S, 12.58%.

Workup

  1. filtrationfiltered
  2. filtrationthe precipitated solid was filtered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-328138924ab94a8b8ff4366662f9e8ea
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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