Diisopropylethylamine → HCID 86644363, compound

HRID 1641382Notes

Reaction equation

HRID 1641382 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=2)[C:5]([F:17])=[CH:4][N:3]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([C@@H:25](N)[CH3:26])=[N:23][CH:24]=1.CC[N:30](C(C)C)C(C)C>CCCCO>[F:17][C:5]1[C:4]([NH2:30])=[N:3][C@H:2]([NH:7][CH:25]([C:22]2[CH:21]=[CH:20][C:19]([F:18])=[CH:24][N:23]=2)[CH3:26])[N:8]([C:9]2[CH:10]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[NH:12][N:13]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 16097531(S)-1-(5-Fluoropyridin-2-yl)ethanamineHCID 178505995HCID 178505995, compound

Product 1

HCID 86644363HCID 86644363, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-5-fluoropyrimidin-4-amine (Method 9; 0.200 g, 0.788 mmol), (S)-1-(5-fluoropyridin-2-yl)ethanamine (Method 6; 0.116 g, 0.828 mmol), and DIEA (0.17 ml, 0.946 mmol) in n-BuOH (2 ml) was heated in a sealed tube at 175° C. for 40 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:EtOAc=1:1) to give the title compound as a white solid (0.175 g, 62%). 1H NMR (400 MHz) 12.47 and 11.98 (s, 1H), 10.15 and 9.27 (s, 1H), 8.48 (s, 1H), 7.89 and 7.81 (s, 1H), 7.65 (m, 1H), 7.42 (b, 1H), 7.20 (b, 1H), 5.76 and 5.64 (s, 1H), 5.00 (m, 1H), 1.85 (m, 1H), 1.44 (d, J=6.8 Hz, 3H), 0.95 (m, 1H), 0.85 (m, 1H), 0.74 (m, 1H), 0.63 (m, 1H). MS: Calcd.: 357. Found: [M+H]+358.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-1e974bfa7a8b41f99f4a10401cf82847
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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