1,5-Naphthalenedisulfonic acid → HCID 87591570, compound

HRID 2112565Notes

Reaction equation

HRID 2112565 reaction equation
[N:1]1([CH2:6][C@H:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])[CH2:8]2)[CH:5]=[N:4][CH:3]=[N:2]1.[C:24]1([S:38]([OH:41])(=[O:40])=[O:39])[C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([S:34]([OH:37])(=[O:36])=[O:35])[C:28]=2[CH:27]=[CH:26][CH:25]=1>CC(C)=O>[C:24]1([S:38]([OH:41])(=[O:40])=[O:39])[C:33]2[CH:32]=[CH:31][CH:30]=[C:29]([S:34]([OH:37])(=[O:36])=[O:35])[C:28]=2[CH:27]=[CH:26][CH:25]=1.[N:1]1([CH2:6][C@H:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])[CH2:8]2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 66661,5-Naphthalenedisulfonic acidHCID 11623906868771-57-7

Product 1

HCID 87591570HCID 87591570, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a stirred solution of Example 42 (700 mg, 2.18 mmol) in acetone (10 ml) was added a solution of naphthalene-1,5-disulfonic acid (860 g, 2.46 mmol) in acetone (10 ml). The solution was stirred at room temperature for 30 min to give a white precipitate. The precipitate was collected by filtration and dried under vacuum to give 1.2 g of the product as a white solid; 1H NMR (D2O, 300 MHz) δ 1.25-1.41 (m, 2H), 1.60-1.70 (m, 2H), 1.88-2.01 (m, 1H), 2.24-2.65 (m, 3H), 3.40-4.06 (m, 6H), 4.21 (d, J=7.5 Hz, 2H), 4.91 (d, J=9.3 Hz, rotomer, 0.9H), 5.10 (d, J=9.1 Hz, rotomer, 0.1H), 5.32-5.49 (m, 1H), 7.67 (t, J=8.7 Hz, 2H), 8.14 (d, J=7.2 Hz, 2H), 8.41 (s, 1H), 8.77 (d, J=9.0 Hz, 2H), 9.12 (s, 1H).

Workup

  1. customto give a white precipitate
  2. filtrationThe precipitate was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-6b5d49bc5a4047c4834e355aebcc1e93
Source dataset
uspto-grants-2009_04
Patent number
US07524844B2

Reaction notes

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