Diisopropylethylamine → HCID 11711016, compound

HRID 75886Notes

Reaction equation

HRID 75886 reaction equation
Cl[C:2]1[N:9]=[C:8]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)[C:7]([Cl:19])=[CH:6][C:3]=1[C:4]#[N:5].CCN(C(C)C)C(C)C.[F:29][C:30]1[CH:31]=[CH:32][C:33]([C@@H:36]([NH2:38])[CH3:37])=[N:34][CH:35]=1>CCCCO.O>[Cl:19][C:7]1[C:8]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)=[N:9][C:2]([NH:38][C@H:36]([C:33]2[CH:32]=[CH:31][C:30]([F:29])=[CH:35][N:34]=2)[CH3:37])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 16097531(S)-1-(5-Fluoropyridin-2-yl)ethanamineHCID 86620607HCID 86620607, compound

Product 1

HCID 11711016HCID 11711016, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A solution of 2,5-dichloro-6-(5-cyclopropyl-1H-pyrazol-3-ylamino)nicotinonitrile (Method 43, 0.60 g, 2.04 mmol), DIEA (0.34 g, 2.65 mmol), and (5)-1-(5-fluoropyridin-2-yl)ethanamine (Method 33; 0.90 g, 6.12 mmol) in n-BuOH was heated to 120° C. for 9 hours. The reaction was then cooled to room temperature, diluted with water (20 ml), and extracted with DCM (2×50 ml). The combined organic fractions were dried over Na2SO4, filtered, and then concentrated. The resulting oil was purified by column chromatography (DCM-MeOH=100:1) to give the title compound (0.42 g, 52%). 1H NMR (400 MHz, CD3OD) δ 8.42 (d, J=2.7 Hz, 1H), 7.61 (s, 1H), 7.51-7.49 (m, 1H), 7.38-7.32 (m, 1H), 6.06 (br s, 1H), 5.28-5.22 (m, 1H), 1.94-1.88 (m, 1H), 1.58 (d, J=6.9 Hz, 3H), 1.01 (br s, 2H), 0.76-0.75 (m, 2H). MS: Calcd.: 397. Found: [M+H]+ 398.

Workup

  1. extractionextracted with DCM (2×50 ml)
  2. dry with materialThe combined organic fractions were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting oil was purified by column chromatography (DCM-MeOH=100:1)

Sources & evidence

ORD record
ord-0ba7a30788ea422dbd5380489485d140
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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