Diisopropylethylamine → HCID 178458670, compound

HRID 450373Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=2)[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=1.Cl.[NH2:22][C@H:23]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=1)[CH2:24][OH:25].C(N(C(C)C)CC)(C)C>CCCCO.C(OCC)(=O)C>[F:32][C:29]1[CH:30]=[CH:31][C:26]([C@@H:23]([NH:22][C:2]2[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=3)[N:7]=2)[CH2:24][OH:25])=[N:27][CH:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 6-chloro-N-(5-isopropoxy-1H-pyrazol-3-yl)-3-nitropyridin-2-amine (Intermediate 7, 0.5 g) and (2R)-2-amino-2-(5-fluoropyridin-2-yl)ethanol hydrochloride (Intermediate 23, 0.45 g) in n-BuOH (10 mL) with diisopropylethylamine (3 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 0.45 g of desired product. MS (electrospray): 418 (M+1) for C18H20FN7O4. 1H NMR (300 MHz, CD3OD) δ ppm 8.50 (s, 1H) 8.20 (d, 1H) 7.60 (s, 1H) 7.45 (s, 1H) 6.30 (s, 1H) 5.70 (s, 1H) 5.45 (m, 1H), 4.60 (m, 1H) 3.90 (m, 2H) 1.30 (d, 6H).

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-e9e18ac10239412992d01c4a7dd7a4d4
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486966B2

Reaction notes

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