Potassium Iodide → HCID 59447030, compound

HRID 1746782Notes

Reaction equation

HRID 1746782 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+].Cl[CH2:36][C:37]([N:39]([CH3:41])[CH3:40])=[O:38]>CN(C=O)C.O>[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:23]=[CH:22][C:21]4[C:17](=[CH:18][N:19]([CH2:36][C:37]([N:39]([CH3:41])[CH3:40])=[O:38])[N:20]=4)[CH:16]=3)=[O:13])[CH:7]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 25182899HCID 25182899, compound

Product 1

HCID 59447030HCID 59447030, 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-chloro-N,N-dimethylacetamide (140 mg; 1.15 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 petroleum ether containing increasing amounts of EtOAc to give the title compound as an off-white solid, together with 6-[(cyclopropylmethyl)(propyl)amino]-N-{1-[2-(dimethylamino)-2-oxoethyl]-1H-indazol-5-yl}pyrimidine-4-carboxamide (Example 115 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 petroleum ether containing
  7. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-e02028d9aaf34498ad8d6e9897fafebe
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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