Chlorosuccinimide → HCID 90419267, compound

HRID 530792Notes

Reaction equation

HRID 530792 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][NH:8][C:9]2[C:10](=[O:28])[N:11]([CH3:27])[N:12]=[C:13]([O:15][CH2:16][C@H:17]3[CH2:19][C@@H:18]3[C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)[CH:14]=2)=[CH:5][C:4]([CH3:29])=[N:3]1.C1C(=O)N([Cl:37])C(=O)C1>ClCCCl.C(#N)C.O>[Cl:37][C:5]1[C:4]([CH3:29])=[N:3][N:2]([CH3:1])[C:6]=1[CH2:7][NH:8][C:9]1[C:10](=[O:28])[N:11]([CH3:27])[N:12]=[C:13]([O:15][CH2:16][C@H:17]2[CH2:19][C@@H:18]2[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=2)[CH:14]=1

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 90454510HCID 90454510, compound

Product 1

HCID 90419267HCID 90419267, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-((1,3-dimethyl-1H-pyrazol-5-yl)methylamino)-2-methyl-6-(((1S,2S)-2-(5-methylpyridin-2-yl)cyclopropyl)methoxy)pyridazin-3(2H)-one (10 mg, 0.025 mmol) in 1,2-Dichloroethane (2.0 mL) was added NCS (4.0 mg, 0.030 mmol). After stirred for 1 h at rt, the reaction mixture was concentrated. The residue was purified by reverse phase chromatography (X bridge Prep C18OBD, 40-60% acetonitrile in water with 10 mmol NH4HCO3 modifier) to obtain product. 1H NMR (400 MHz, MeOD) δ 8.21 (s, 1H), 7.53 (d, 1H), 7.14 (d, 1H), 5.91 (s, 1H), 4.42 (s, 2H), 4.21-4.16 (m, 1H), 4.11-4.06 (m, 1H), 3.79 (s, 3H), 3.63 (s, 3H), 2.31 (s, 3H), 2.19 (s, 3H), 2.12-2.06 (m, 1H), 1.82-1.79 (m, 1H), 1.25-1.20 (m, 1H), 1.10-1.05 (m, 1H); LRMS m/z (M+H) 429.1 found, 429.17 required.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto obtain product

Sources & evidence

ORD record
ord-37199815ffa54a35b498b8e3e77747f9
Source dataset
uspto-grants-2016_05
Patent number
US09353104B2

Reaction notes

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