Benzenesulfonyl chloride → HCID 58168028, compound

HRID 1029251Notes

Reaction equation

HRID 1029251 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:18]=[CH:17][N:16]=[C:15]3[C:10]=2[C:11]2[CH:23]=[CH:22][CH:21]=[CH:20][C:12]=2[C:13](=[O:19])[NH:14]3)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>COCCOC>[O:19]=[C:13]1[C:12]2[CH:20]=[CH:21][CH:22]=[CH:23][C:11]=2[C:10]2[C:15](=[N:16][CH:17]=[CH:18][C:9]=2[NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)(=[O:41])=[O:40])=[CH:7][CH:6]=2)[NH:14]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58168047HCID 58168047, compound

Product 1

HCID 58168028HCID 58168028, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

340 (40 mg, 0.13 mmol), DIEA (34 mg, 0.26 mmol), and benzenesulfonyl chloride (47 mg, 0.26 mmol) were suspended in DME (2 mL), and stirred for 4 h at room temperature. The precipitate formed during the reaction was filtered, washed with EtOAc, and dried under vacuum to provide 341 (20 mg, 34% yield) as a solid. LC-MS (M+H=443, obsd.=443).

Workup

  1. customThe precipitate formed during the reaction
  2. filtrationwas filtered
  3. washwashed with EtOAc
  4. customdried under vacuum

Sources & evidence

ORD record
ord-22176d27417f4a458387d71e1b7798e7
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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