Chlorosuccinimide → 6-(4-chloro-3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

HRID 80856Notes

Reaction equation

HRID 80856 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([N:9]3[CH2:41][CH2:40][C:12]4[N:13]=[C:14]([C:19]5[C:27]([CH3:28])=[CH:26][CH:25]=[C:24]6[C:20]=5[C:21]([CH3:39])=[N:22][N:23]6[S:29]([C:32]5[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=5)(=[O:31])=[O:30])[N:15]=[C:16]([O:17][CH3:18])[C:11]=4[CH2:10]3)[N:6]([CH3:42])[N:5]=2)[CH2:3][CH2:2]1.[Cl:43]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:43][C:8]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][N:6]([CH3:42])[C:7]=1[N:9]1[CH2:41][CH2:40][C:12]2[N:13]=[C:14]([C:19]3[C:27]([CH3:28])=[CH:26][CH:25]=[C:24]4[C:20]=3[C:21]([CH3:39])=[N:22][N:23]4[S:29]([C:32]3[CH:33]=[CH:34][C:35]([CH3:36])=[CH:37][CH:38]=3)(=[O:31])=[O:30])[N:15]=[C:16]([O:17][CH3:18])[C:11]=2[CH2:10]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 712405876-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Product 1

HCID 712388626-(4-chloro-3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (7.0 g, 11.99 mmol) in DCM (120 mL) was added N-chlorosuccinimide (1.76 g, 13.19 mmol) at room temperature, and the reaction mixture was stirred overnight. The mixture was then concentrated and the residue was directly purified by FCC (20-100% EtOAc/heptane) to provide 6-(4-chloro-3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 619.9 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated
  2. customthe residue was directly purified by FCC (20-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-9636fa2813a745c0a88225e634b6f6ba
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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