Dimethylformamide → HCID 66576288, compound

HRID 1409364Notes

Reaction equation

HRID 1409364 reaction equation
[OH:1][CH:2]([C:6]1[O:10][N:9]=[C:8]([C:11]([OH:13])=O)[CH:7]=1)[CH:3]([CH3:5])[CH3:4].[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[CH:7]=[C:6]([CH:2]([OH:1])[CH:3]([CH3:4])[CH3:5])[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 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 86714640HCID 86714640, compound

Product 1

HCID 66576288HCID 66576288, compoundYield 1.8%

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-(1-hydroxy-2-methylpropyl)isoxazole-3-carboxylic acid (2.160 mmol, 0.4 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluoro-benzonitrile (1.800 mmol, 0.502 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 2 M Na2CO3, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and preparative HPLC, respectively. 0.0146 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 0.89 (d, 3H), 0.92-0.98 (m, 3H), 1.26 (d, 3H), 2.01-2.13 (m, 1H), 4.28-4.45 (m, 2H), 4.51-4.64 (m, 2H), 6.53 (d, 1H), 6.79 (d, 1H), 7.68-7.77 (m, 2H), 7.91 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customthe phases were separated
  3. washthe organic phase was washed with 2 M 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-9d93ba31efe14cbfaedbe03c58648dfe
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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