Methanesulfonic Acid → HCID 178505350, compound

HRID 1644227Notes

Reaction equation

HRID 1644227 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13](=[NH:34])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([O:29][CH2:30][CH2:31][CH2:32][NH2:33])=[CH:21][CH:20]=2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[CH3:35][S:36]([OH:39])(=[O:38])=[O:37]>CCO>[CH3:35][S:36]([OH:39])(=[O:38])=[O:37].[CH3:35][S:36]([OH:39])(=[O:38])=[O:37].[NH2:1][C:2]1[C:3]([C:10]([NH:12][C:13](=[NH:34])[NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([O:29][CH2:30][CH2:31][CH2:32][NH2:33])=[CH:21][CH:20]=2)=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178512151HCID 178512151, compound

Product 2

HCID 6395Methanesulfonic AcidHCID 178505350HCID 178505350, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of carboxamide 71 (120 mg, 0.247 mmole) in EtOH (10 mL) was added methanesulfonic acid (48 mg, 0.495 mmole) at room temperature and the reaction mixture was stirred for 15 min. The solvent was removed in vacuo. The residue was dissolved in water (10 mL) and lyophilized to afford methanesulfonic acid salt 72 (160 mg, 95%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 10.44 (s, 1H), 9.15 (br s, 1H), 8.86 (br s, 1H), 8.72 (br s, 1H), 8.22 (dd, J=8.1, 0.9, Hz, 1H), 8.03 (d, J=8.1 Hz, 1H), 7.80 (br s, 4H), 7.61-7.49 (m, 3H), 7.42 (br s, 2H), 7.28 (d, J=7.8 Hz, 1H), 6.89 (d, J=7.8 Hz, 1H), 4.22 (t, J=5.7 Hz, 2H), 3.35 3.33 (m, 2H), 3.17 2.99 (m, 4H), 2.32 (s, 6H), 2.20-2.10 (m, 2H), 1.68 (br s, 4H); ESI-MS m/z 485 [C23H29ClN8O2+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water (10 mL)

Sources & evidence

ORD record
ord-dc77e6531e68437db4cfa367ea0915dd
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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