Ethanesulfonylchloride, 2-chloro- → HCID 69842640, compound
Reaction equation
Cl[CH2:2][CH2:3]S(Cl)(=O)=O.Cl.[NH:9]1[CH:13]=[C:12]([CH2:14][N:15]2[C:21]3[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:20]=3[CH2:19][N:18]([S:28]([CH3:31])(=[O:30])=[O:29])[C@H:17]([CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:16]2)[N:11]=[CH:10]1.CCN([CH:45]([CH3:47])[CH3:46])C(C)C.[C:48]([O-:51])(O)=[O:49].[Na+]>ClCCl.C(Cl)(Cl)Cl>[C:26]([C:24]1[CH:23]=[CH:22][C:21]2[N:15]([CH2:14][C:12]3[N:11]=[CH:10][N:9]([C:48]([O:51][C:20]([CH3:25])([CH3:21])[CH3:19])=[O:49])[CH:13]=3)[CH2:16][C@@H:17]([CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:18]([S:28]([C:31]3[CH:3]=[CH:2][CH:46]=[CH:45][CH:47]=3)(=[O:29])=[O:30])[CH2:19][C:20]=2[CH:25]=1)#[N:27]Participants
7
Procedure
2-Chloroethanesulfonyl chloride (1.85 g, 11.4 mmol) was added to a solution of Compound C of Example 248 (1.0 g, 3.79 mmol) and DIEA (2.6 mL, 15.16 mmol) in dichloromethane (16 mL) at 0° C. under argon. After stirring for 16 hr, the reaction was diluted with chloroform (20 mL) and NaHCO3 (5 mL). The layers were separated, the aqueous layer was extracted with chloroform (2×50 mL). The combined organic extracts were washed with NaHCO3 (2×20 mL) and brine (2×50 mL), dried over MgSO4, filtered and concentrated, to afford Compound A (1.55 g, 116.5%).
Workup
- customThe layers were separated
- extractionthe aqueous layer was extracted with chloroform (2×50 mL)
- washThe combined organic extracts were washed with NaHCO3 (2×20 mL) and brine (2×50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e474d27757da45809695accda966ef56
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455523B1
Reaction notes
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