Methanesulfonic Acid → HCID 178505350, compound

HRID 2036260Notes

Reaction equation

HRID 2036260 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-f410ada1abb24e418c087584fd043a53
Source dataset
uspto-grants-2013_11
Patent number
US08575176B2

Reaction notes

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