Chlorosuccinimide → (S)-tert-butyl (1-(5-amino-6-chloro-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate

HRID 2170389Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:26]2[CH:27]=[CH:28][C:29]([Cl:41])=[C:30]3[C:34]=2[N:33]([CH3:35])[N:32]=[C:31]3[NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[C:5]([C@@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([F:17])[CH:11]=2)=[N:6][CH:7]=1.C1C(=O)N([Cl:49])C(=O)C1>C(#N)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:26]2[CH:27]=[CH:28][C:29]([Cl:41])=[C:30]3[C:34]=2[N:33]([CH3:35])[N:32]=[C:31]3[NH:36][S:37]([CH3:40])(=[O:38])=[O:39])[C:5]([C@@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:9][C:10]2[CH:11]=[C:12]([F:17])[CH:13]=[C:14]([F:16])[CH:15]=2)=[N:6][C:7]=1[Cl:49]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 49A (300 mg, 0.49 mmol) in 5 mL of acetonitrile was cooled to 0° C. and treated with NCS (0.49 mmol). The reaction was heated to 60° C. overnight. The reaction mixture was partitioned with EtOAc and aqueous saturated NaHCO3, then washed with brine. The organic layer were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography to provide the title compound. MS (m/z) 641 [M+H]+.

Workup

customThe reaction mixture was partitioned with EtOAc and aqueous saturated NaHCO3
washwashed with brine
dry with materialThe organic layer were dried over MgSO4
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-84e5deec1fb34e0b955167add98fb33b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09050344B2

Reaction notes

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