Potassium Iodide → HCID 59446829, compound

HRID 1946804Notes

Reaction equation

HRID 1946804 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:24][CH2:25][CH3:26])[C:6]2[N:11]=[CH:10][N:9]=[C:8]([C:12]([NH:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[NH:20][N:19]=[CH:18]4)=[O:13])[CH:7]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:36][C:37]([NH2:39])=[O:38]>CN(C=O)C.O>[NH2:39][C:37](=[O:38])[CH2:36][N:20]1[C:21]2[C:17](=[CH:16][C:15]([NH:14][C:12]([C:8]3[CH:7]=[C:6]([N:5]([CH2:4][CH:1]4[CH2:3][CH2:2]4)[CH2:24][CH2:25][CH3:26])[N:11]=[CH:10][N:9]=3)=[O:13])=[CH:23][CH:22]=2)[CH:18]=[N:19]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 25182899HCID 25182899, compound

Product 1

HCID 59446829HCID 59446829, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-((cyclopropylmethyl)(propyl)amino)-N-(1H-indazol-5-yl)pyrimidine-4-carboxamide (Example 45, 350 mg; 1 mmol) in DMF (4 ml) was treated with potassium carbonate (140 mg; 1 mmol), potassium iodide (1 mg) and 2-bromoacetamide (160 mg; 1.16 mmol). After stirring at RT for 72 hours the mixture was poured in water (20 ml) and stirred at RT for 1 hour. The solid was removed by filtration, washed with water and dried. The residue was purified by column chromatography (silica) eluting with EtOAc containing increasing amounts of MeOH to give the title compound as an off-white solid, together with N-[2-(2-amino-2-oxoethyl)-2H-indazol-5-yl]-6-[(cyclopropylmethyl)(propyl)amino]pyrimidine-4-carboxamide (Example 118 below).

Workup

  1. stirringstirred at RT for 1 hour
  2. customThe solid was removed by filtration
  3. washwashed with water
  4. customdried
  5. customThe residue was purified by column chromatography (silica)
  6. washeluting with EtOAc containing
  7. temperatureincreasing amounts of MeOH

Sources & evidence

ORD record
ord-ead9599d04254656b96dd0c51ffc1b5a
Source dataset
uspto-grants-2013_03
Patent number
US08399448B2

Reaction notes

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