Chlorosuccinimide → HCID 178467170, compound

HRID 80855Notes

Reaction equation

HRID 80855 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([N:9]3[CH2:36][CH2:35][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]([CH3:34])=[N:27][NH:28]6)[N:15]=[C:16]([N:17]5[CH2:20][CH:19]([O:21][CH2:22][CH3:23])[CH2:18]5)[C:11]=4[CH2:10]3)[N:6]([CH3:37])[N:5]=2)[CH2:3][CH2:2]1.[Cl:38]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:38][C:8]1[C:4]([CH:1]2[CH2:2][CH2:3]2)=[N:5][N:6]([CH3:37])[C:7]=1[N:9]1[CH2:36][CH2:35][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]([CH3:34])=[N:27][NH:28]4)[N:15]=[C:16]([N:17]3[CH2:18][CH:19]([O:21][CH2:22][CH3:23])[CH2:20]3)[C:11]=2[CH2:10]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 178467169HCID 178467169, compound

Product 1

HCID 178467170HCID 178467170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1H-indazol-4-yl)-4-(3-ethoxyazetidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (30 mg, 0.060 mmol) in DCM (2 mL) was added N-chlorosuccinimide (9.64 mg, 0.072 mmol) at room temperature. The mixture was stirred for 30 min then concentrated. The residue was purified by reverse phase HPLC (C18, 10-100% acetonitrile-H2O with 0.1% NH4OH) to give 6-(4-chloro-3-cyclopropyl-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1H-indazol-4-yl)-4-(3-ethoxyazetidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.43 (d, J=8.46 Hz, 1H), 7.30 (d, J=8.59 Hz, 1H), 4.49 (dd, J=6.63, 9.41 Hz, 2H), 4.35-4.45 (m, 3H), 4.14 (dd, J=4.04, 10.36 Hz, 2H), 3.66 (s, 3H), 3.46-3.55 (m, 4H), 2.89 (t, J=5.68 Hz, 2H), 2.27 (s, 3H), 2.04 (s, 3H), 1.81-1.88 (m, 1H), 1.19 (t, J=7.01 Hz, 3H), 0.76-0.93 (m, 4H); MS (ESI+) m/z 533.4 (M+H)+.

Workup

  1. concentrationthen concentrated
  2. customThe residue was purified by reverse phase HPLC (C18, 10-100% acetonitrile-H2O with 0.1% NH4OH)

Sources & evidence

ORD record
ord-6c33de29274e41a5b85534d69c45c015
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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