Sodium Sulfite → HCID 58504870, compound

HRID 537410Notes

Reaction equation

HRID 537410 reaction equation
C(OC([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([S:17]([OH:19])=[O:18])[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.[Li].C1C(=O)N(Cl)C(=O)C1.[NH2:29][CH:30]([C:41]([N:43]1[CH2:48][CH2:47][CH:46]([CH3:49])[CH2:45][CH2:44]1)=[O:42])[CH2:31][CH2:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[C:36]#[N:37].[O-]S([O-])=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[C:36]([C:35]1[CH:34]=[C:33]([CH2:32][CH2:31][CH:30]([NH:29][S:17]([C:12]2[C:11]3[CH:10]=[CH:9][NH:8][C:16]=3[CH:15]=[CH:14][CH:13]=2)(=[O:18])=[O:19])[C:41]([N:43]2[CH2:44][CH2:45][CH:46]([CH3:49])[CH2:47][CH2:48]2)=[O:42])[CH:40]=[CH:39][CH:38]=1)#[N:37]

Participants

7

Reactant 4

HCID 24437Sodium SulfiteHCID 31398ChlorosuccinimideHCID 66996980HCID 66996980, compoundHCID 131731953HCID 131731953, compound

Product 1

HCID 58504870HCID 58504870, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 0.29 g (0.77 mmol) of lithum 1-(tert-butoxycarbonyl)-1H-indole-4-sulfinic acid stirring in 1 mL of THF is added 62 mg (0.47 mmol) of NCS. After stirring for 5 minutes, 0.10 g (0.31 mmol) of 3-[3-amino-4-(4-methylpiperidin-1-yl)-4-oxobutyl]benzonitrile is added and the mixture is stirred for 4 h when 10% Na2SO3 and CH2Cl2 are added. The organic phase is dried over Na2SO4, filtered, and concentrated. Preparative TLC (33% EtOAc in hexanes) provides 70 mg (40%) of the sulfonamide. This material (30 mg, 0.053 mmol) in 1 mL of CH2Cl2 is treated with 0.2 mL of TFA for 90 minutes. The mixture is concentrated and purified by preparative TLC (5% MeOH in CH2Cl2) to provide 21 mg (85%) of Example 71. ESI MS Calc. 464.2; Found: 465.7 (M+H)+.

Workup

  1. additionare added
  2. dry with materialThe organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2a1c153ff3dc4c1a9ccbdfe81a4810fc
Source dataset
uspto-grants-2014_10
Patent number
US08859814B2

Reaction notes

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