Diisopropylethylamine → HCID 178458616, compound

HRID 415428Notes

Reaction equation

HRID 415428 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([F:14])=[C:4](Cl)[N:3]=1.[CH:16]([O:19][C:20]1[NH:24][N:23]=[C:22]([NH2:25])[CH:21]=1)([CH3:18])[CH3:17].CCN(C(C)C)C(C)C>CCCCO>[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])[C:5]([F:14])=[C:4]([NH:25][C:22]2[CH:21]=[C:20]([O:19][CH:16]([CH3:18])[CH3:17])[NH:24][N:23]=2)[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 86624844N-(2,6-dichloro-5-fluoro-pyrimidin-4-yl)-N-methyl-methanesulfonamideHCID 1784587215-Isopropoxy-1H-pyrazol-3-amine

Product 1

HCID 178458616HCID 178458616, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-(2,6-dichloro-5-fluoro-pyrimidin-4-yl)-N-methyl-methanesulfonamide (Method 21, 440 mg, 1.6 mmol) in n-BuOH (3 ml) was added 5-isopropoxy-1H-pyrazol-3-ylamine (227 mg, 1.6 mmol) and DIPEA (207 mg). The mixture was heated at 70° C. overnight. LC/MS showed the completion of the reaction. The solvent was evaporated and the residue was dissolved in DCM, which was then washed by aqueous NaHCO3, dried and concentrated. Flash chromatography was performed with EtOAc/Hex (50%) as eluent. A colourless solid (280 mg) was obtained, yield 46%. 1H-NMR (300 MHz, CD3OD) 5.84 (s, 0.8H), 4.61 (m, 1H), 3.32 (s, 3H), 3.27 (s, 3H), 1.36 (d, J=6.0; 6H). MS (ES+) m/z 378.86, 380.86 [MH+]. MS (ES−) m/z 376.88, 378.87 [M−].

Workup

  1. customthe completion of the reaction
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwhich was then washed by aqueous NaHCO3
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6cd2cf9d7dfe4427a3f2c649af704b16
Source dataset
uspto-grants-2012_01
Patent number
US08088784B2

Reaction notes

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