Diisopropylethylamine → HCID 86649277, compound

HRID 450365Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=1.Cl.[F:21][C:22]1[CH:23]=[N:24][C:25]([C@@H:28]([NH2:30])[CH3:29])=[N:26][CH:27]=1.C(N(C(C)C)CC)(C)C>CCCCO.C(OCC)(=O)C>[CH:14]1([C:12]2[NH:11][N:10]=[C:9]([NH:8][C:6]3[C:5]([N+:17]([O-:19])=[O:18])=[CH:4][CH:3]=[C:2]([NH:30][C@H:28]([C:25]4[N:26]=[CH:27][C:22]([F:21])=[CH:23][N:24]=4)[CH3:29])[N:7]=3)[CH:13]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-3-nitropyridin-2-amine (Intermediate 9, 0.5 g) and [(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amine hydrochloride (Intermediate 15, 0.35 g) in n-BuOH (10 mL) with diisopropylethylamine (1 mL) was stirred at 70° C. for 4 hours. The resulting mixture was diluted with ethyl acetate (20 mL), and washed with brine (10 mL×3). The organic layer was dried and concentrated. The resulting residue was separated by silica gel column (Hexane/Ethyl acetate) to yield 0.5 g of desired product. MS (electrospray): 385 (M+1) for C17H18FN8O2. 1H NMR (300 MHz, CD3OD) δ ppm 8.70 (s, 2H) 8.20 (d, 1H) 6.40 (m, 1H) 6.20 (d, 1H) 5.45 (m, 1H), 1.90 (m, 1H) 1.70 (d, 3H) 1.05 (m, 2H) 0.90 (m, 2H).

Workup

washwashed with brine (10 mL×3)
customThe organic layer was dried
concentrationconcentrated
customThe resulting residue was separated by silica gel column (Hexane/Ethyl acetate)

Sources & evidence

ORD record: ord-03a6ab8953534904ae4deddc29ac6a2c
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486966B2

Reaction notes

Loading…