Hydrochloric Acid → HCID 66892013, compound

HRID 1162037Notes

Reaction equation

HRID 1162037 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[NH:10][S:11]([C:14]1[CH:15]=[C:16]([C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH:27]([CH3:31])[CH2:26]2)=O)[C:17]2[O:21][CH:20]=[CH:19][C:18]=2[CH:22]=1)(=[O:13])=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3].[ClH:38]>C1COCC1>[ClH:38].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[NH:10][S:11]([C:14]1[CH:15]=[C:16]([CH2:23][N:25]2[CH2:30][CH2:29][NH:28][CH:27]([CH3:31])[CH2:26]2)[C:17]2[O:21][CH:20]=[CH:19][C:18]=2[CH:22]=1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 66893658HCID 66893658, compound

Product 1

HCID 66892013HCID 66892013, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the obtained 7-(3-methyl-piperazin-1-carbonyl)-benzofuran-5-sulfonic acid (2-methoxy-5-methyl-phenyl)-amide (30 mg, 0.07 mmol; Step 1) was added LiAlH4 (9.0 mg, 0.24 mmol) in dry THF (4 mL) and the mixture was warmed to reflux. After 1 h, HPLC analysis showed 15% product and the remaining impurities. Added mixture to 2 M HCl, concentrated and purified by preparative HPLC (Gilson; gradient of 30-70% MeCN). The pure fractions were stripped, HCl/ether added and concentrated to give the title compound as a colourless solid. Yield: 1.3 mg (5%). HPLC 90% RT=1.17 min (System A; 30-80% MeCN over 3 min), 1.13 min (System C; 2-95% MeCN over 2 min). 1H NMR (400 MHz, methanol-d4) δ ppm 1.29 (d, J=7.0 Hz, 2H) 2.21 (s, 3H) 2.72 (m, 1H) 2.86 (m, 1H) 3.38 (s, 4H) 3.43-3.64 (m, 4H) 4.30 (d, J=6.59 Hz, 2H) 6.62 (d, J=8.30 Hz, 1H) 6.81-6.88 (m, 1H) 6.99 (d, J=2.44 Hz, 1H) 7.25 (d, J=1.95 Hz, 1H) 7.76 (br s, 1H) 7.94 (d, J=2.20 Hz, 1H) 8.08 (d, J=1.71 Hz, 1H). MS (ESI) for C22H27N3O4S m/z 430 (M+H).

Workup

  1. temperaturethe mixture was warmed to reflux
  2. concentrationconcentrated
  3. custompurified by preparative HPLC (Gilson; gradient of 30-70% MeCN)
  4. additionHCl/ether added
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-77d9d7d2145140afb373ae5d00c31f49
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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