Diisopropylethylamine → HCID 178455878, compound

HRID 450382Notes

Reaction equation

HRID 450382 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.[F:21][C:22]1[CH:23]=[CH:24][C:25]([C@@H:28](N)[CH2:29][CH3:30])=[N:26][CH:27]=1.C([N:35](C(C)C)CC)(C)C>CCCCO.C(OCC)(=O)C>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C@H:28]([C:4]2[CH:3]=[C:2]([NH2:35])[N:7]=[C:6]([NH:8][C:9]3[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[NH:11][N:10]=3)[C:5]=2[N+:18]([O-:20])=[O:19])[CH2:29][CH3:30])=[N:26][CH:27]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 68779594[(1S)-1-(5-fluoropyridin-2-yl)propyl]amine2×HCID 178458609HCID 178458609, compound2×

Product 1

HCID 178455878HCID 178455878, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

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 [(15)-1-(5-fluoropyridin-2-yl)propyl]amine (Intermediate 35, 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): 416 (M+1) for C19H22FN7O3.

Workup

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

Sources & evidence

ORD record
ord-db70e1fa0a854501b02e6050ccb8c9c0
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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