(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile → HCID 86714647, compound

HRID 1409385Notes

Reaction equation

HRID 1409385 reaction equation
[CH3:1][C:2]([CH3:12])=[CH:3][N:4]1[CH:8]=[CH:7][C:6]([C:9]([OH:11])=O)=[N:5]1.[NH2:13][C@@H:14]([CH3:31])[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[C:27]([F:29])[C:24]([C:25]#[N:26])=[C:23]([Cl:30])[CH:22]=2)=[N:17]1>C(Cl)Cl>[Cl:30][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[CH:20][N:16]([CH2:15][C@@H:14]([NH:13][C:9]([C:6]3[CH:7]=[CH:8][N:4]([CH:3]=[C:2]([CH3:1])[CH3:12])[N:5]=3)=[O:11])[CH3:31])[N:17]=2)[CH:28]=[C:27]([F:29])[C:24]=1[C:25]#[N:26]

Participants

4

Reactant 2

HCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 86714648HCID 86714648, compound

Product 1

HCID 86714647HCID 86714647, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 1-(2-methyl-prop-1-en-1-yl)-1H-pyrazole-3-carboxylic acid (1.076 mmol, 179 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluoro-benzonitrile (0.897 mmol, 250 mg) using DCM (5 ml) as the solvent. The mixture was diluted with DCM, washed with 1M Na2CO3 and water. The organic phase was dried, filtered and evaporated. The product was purified by flash chromatography. 298 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.12 (d, 3H), 1.80 (d, 3H), 1.84 (d, 3H), 4.27-4.50 (m, 3H), 6.66 (d, 1H), 6.77-6.80 (m, 1H), 7.01 (d, 1H), 7.83 (d, 1H), 7.85-7.89 (m, 2H), 7.95-7.98 (m, 1H), 8.15 (d, 1H).

Workup

  1. customThe title compound was prepared
  2. washwashed with 1M Na2CO3 and water
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-3edac45831404f27a543938ecc84dfb1
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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