Dimethylformamide → HCID 66576290, compound

HRID 1409370Notes

Reaction equation

HRID 1409370 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[O:10][N:9]=[C:8]([C:11]([OH:13])=O)[N:7]=2)=[N:2]1.[NH2:14][C@@H:15]([CH3:32])[CH2:16][N:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:29]=[C:28]([F:30])[C:25]([C:26]#[N:27])=[C:24]([Cl:31])[CH:23]=2)=[N:18]1.CN(C=O)C>O.CCOC(C)=O>[Cl:31][C:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][N:17]([CH2:16][C@@H:15]([NH:14][C:11]([C:8]3[N:7]=[C:6]([C:3]4[CH:4]=[CH:5][O:1][N:2]=4)[O:10][N:9]=3)=[O:13])[CH3:32])[N:18]=2)[CH:29]=[C:28]([F:30])[C:25]=1[C:26]#[N:27]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 63383100HCID 63383100, compoundHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile

Product 1

HCID 66576290HCID 66576290, compoundYield 0.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 5-(isoxazol-3-yl)-1,2,4-oxadiazole-3-carboxylic acid (1.933 mmol, 0.35 g) and (S)-4-(1-(2-amino-propyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (1.610 mmol, 0.449 g) using DMF (10 ml) as the solvent. The reaction mixture was diluted with water and EtOAc, the phases were separated and the organic phase was washed with 2M Na2CO3, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and preparative HPLC, respectively. 0.0065 g of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 1.26 (d, 3H), 4.28 (dd, 1H), 4.46 (dd, 1H), 4.56-4.66 (m, 1H), 6.63 (d, 1H), 6.82 (d, 1H), 7.51 (d, 1H), 7.64 (dd, 1H), 7.84-7.86 (m, 1H), 7.88 (d, 1H), 8.51 (d, 1H).

Workup

  1. customThe title compound was prepared
  2. customthe phases were separated
  3. washthe organic phase was washed with 2M Na2CO3, water and brine
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography and preparative HPLC

Sources & evidence

ORD record
ord-93f1a3f14b0a4379a4a885d77de09ebe
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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