Chlorosuccinimide → HCID 71244814, compound

HRID 80862Notes

Reaction equation

HRID 80862 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([N:9]3[CH2:46][CH2:45][C:12]4[N:13]=[C:14]([C:24]5[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]6[C:25]=5[C:26]([CH3:44])=[N:27][N:28]6[S:34]([C:37]5[CH:43]=[CH:42][C:40]([CH3:41])=[CH:39][CH:38]=5)(=[O:36])=[O:35])[N:15]=[C:16]([N:17]5[CH2:22][CH2:21][O:20][CH2:19][C@H:18]5[CH3:23])[C:11]=4[CH2:10]3)[N:6]([CH2:47][CH3:48])[N:5]=2)[CH2:3][CH2:2]1.C1C(=O)N([Cl:56])C(=O)C1>C(Cl)Cl>[Cl:56][C:8]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][N:6]([CH2:47][CH3:48])[C:7]=1[N:9]1[CH2:46][CH2:45][C:12]2[N:13]=[C:14]([C:24]3[C:32]([CH3:33])=[CH:31][CH:30]=[C:29]4[C:25]=3[C:26]([CH3:44])=[N:27][N:28]4[S:34]([C:37]3[CH:38]=[CH:39][C:40]([CH3:41])=[CH:42][CH:43]=3)(=[O:35])=[O:36])[N:15]=[C:16]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][C@H:18]3[CH3:23])[C:11]=2[CH2:10]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 71240671(R)-4-(6-(3-cyclopropyl-1-ethyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylmorpholine

Product 1

HCID 71244814HCID 71244814, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-4-(6-(3-cyclopropyl-1-ethyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylmorpholine (0.075 g, 0.112 mmol) in DCM (2.2 mL) was added NCS (0.016 g, 0.124 mmol). After 1 h the solvent was removed under reduced pressure and the residue purified directly by FCC (20-80% EtOAc/heptanes) to provide the title compound (R)-4-(6-(4-chloro-3-cyclopropyl-1-ethyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylmorpholine. MS (ESI+) m/z 701.1 (M+H)+.

Workup

  1. customAfter 1 h the solvent was removed under reduced pressure
  2. customthe residue purified directly by FCC (20-80% EtOAc/heptanes)

Sources & evidence

ORD record
ord-2ffc75a8fcdc44498cc56ca242740a03
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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