Benzenesulfonyl chloride → HCID 178480493, compound

HRID 874444Notes

Reaction equation

HRID 874444 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][N:5]([CH3:27])[C:6]2[C:7]=1[CH:8]=[CH:9][C:10]1[N:19]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:18][CH:17]=[C:12]3[NH:13][C:14](=[O:16])[C:15]=2[C:11]=13.C(N(CC)C(C)C)(C)C.[C:37]1([S:43](Cl)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>ClCCl>[F:26][C:23]1[CH:22]=[CH:21][C:20]([N:19]2[C:10]3=[C:11]4[C:15](=[C:6]5[N:5]([CH3:27])[CH:4]=[CH:3][C:2]([NH:1][S:43]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)(=[O:45])=[O:44])=[C:7]5[CH:8]=[CH:9]3)[C:14](=[O:16])[NH:13][C:12]4=[CH:17][CH2:18]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 81531Diisopropylethylamine2×HCID 178480427HCID 178480427, compound

Product 1

HCID 178480493HCID 178480493, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stock solution of Example 23e and N,N-diisopropylethylamine (0.08 M and 0.16 M in dichloromethane, respectively, 500 μL, 0.042 mmol Example 23e and 0.083 mmol N,N-diisopropylethylamine), and benzenesulfonyl chloride (0.40 M in dichloromethane, 239 μL, 0.096 mmol) were mixed and stirred at ambient temperature overnight. The reaction mixture was concentrated, dissolved in methanol (1 mL) and injected on the reverse phase HPLC(C8, acetonitrile/water (0.1% TFA), 5-100%) to yield the title compound as an impure mixture.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in methanol (1 mL)

Sources & evidence

ORD record
ord-374000863cb74b4498972dd0597fda3b
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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