N-Acetylsulfanilyl chloride → HCID 178474289, compound

HRID 874445Notes

Reaction equation

HRID 874445 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][N:5]([CH3:27])[C:6]2[C:7]=1C=N[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.[CH:28](N(CC)C(C)C)(C)[CH3:29].[C:37]([NH:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1)(=[O:39])[CH3:38]>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:47]([C:44]6[CH:45]=[CH:46][C:41]([NH:40][C:37](=[O:39])[CH3:38])=[CH:42][CH:43]=6)(=[O:49])=[O:48])=[C:7]5[CH:28]=[CH:29]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 8481N-Acetylsulfanilyl chlorideHCID 81531Diisopropylethylamine2×HCID 178480438HCID 178480438, compound

Product 1

HCID 178474289HCID 178474289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stock solution of Example 14e and N,N-diisopropylethylamine (0.08 M and 0.16 M in dichloromethane, respectively, 500 μL, 0.042 mmol Example 14e and 0.083 mmol N,N-diisopropylethylamine), and 4-acetamidobenzene-1-sulfonyl 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. The material was dissolved in methanol (1 mL) and manually injected into the HPLC(C8, acetonitrile/water (0.1% TFA), 5-100%) to give 0.0071 g (32%) of the title compound as the TFA salt. 1H NMR (400 MHz, DMSO-d6/D2O) δ 7.75 (q, J=9.16 Hz, 4H), 7.57 (s, 1H), 7.48 (d, J=2.44 Hz, 1H), 7.11 (d, J=8.54 Hz, 1H), 7.02 (s, 1H), 6.95 (dd, J=8.54, 2.44 Hz, 1H), 6.80 (m, J=8.85, 8.85 Hz, 2H), 6.37 (m, 2H), 4.97 (s, 1H), 4.12 (m, 1H), 4.04 (s, 3H), 2.06 (s, 3H). MS (APCI+) m/z 558.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-b17c65a979434a5099b61cd9f61ac8a2
Source dataset
uspto-grants-2015_03
Patent number
US08980879B2

Reaction notes

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