Diisopropylethylamine → 6-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (2-cyclohexyl-5-pyridin-2-yl-2H-pyrazol-3-yl)-amide

HRID 1260315Notes

Reaction equation

HRID 1260315 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([OH:12])=O)[C:7]([NH:13][C:14]3[CH:15]=[N:16][CH:17]=[N:18][CH:19]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[CH:20]1([N:26]2[C:30]([NH2:31])=[CH:29][C:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[N:27]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(C(C)C)C(C)C)C.CCCP(=O)=O>>[CH:20]1([N:26]2[C:30]([NH:31][C:10]([C:8]3[C:7]([NH:13][C:14]4[CH:15]=[N:16][CH:17]=[N:18][CH:19]=4)=[CH:6][CH:5]=[C:4]([CH:1]4[CH2:2][CH2:3]4)[N:9]=3)=[O:12])=[CH:29][C:28]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[N:27]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 16167369Propylphosphoric anhydrideHCID 583680496-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acidHCID 672999142-cyclohexyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine

Product 1

HCID 533284476-Cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (2-cyclohexyl-5-pyridin-2-yl-2H-pyrazol-3-yl)-amideYield 29%

Procedure

To a suspension of 6-cyclopropyl-3-(pyrimidin-5-ylamino)-pyridine-2-carboxylic acid (50 mg, 0.2 mmol; intermediate A-5) at r.t under an argon atmosphere were added 2-cyclohexyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine (47 mg, 0.2 mmol) and N-ethyldiisopropylamine (0.1 ml, 0.6 mmol). The yellow suspension was cooled to 0°, and propylphosphonic anhydride (0.31 ml, 1 mmol; 50% in AcOEt) was added. The suspension was stirred at 0° for 30 min. and at r.t overnight. The solvent was evaporated. After silica gel chromatography using a CH2Cl2/MeOH gradient, the product was obtained as yellow solid in 29% yield. MS: M=481.3 (M+H)+

Workup

  1. temperatureThe yellow suspension was cooled to 0°
  2. customThe solvent was evaporated
  3. customthe product was obtained as yellow solid in 29% yield

Sources & evidence

ORD record
ord-099750adcb8b4e4dac8143f5ef028adb
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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