(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile → HCID 66576844, compound

HRID 1409418Notes

Reaction equation

HRID 1409418 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]([CH3:30])[CH2:15][N:16]1[CH:20]=[CH:19][C:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[C:23]([Cl:29])[CH:22]=2)=[N:17]1>C(Cl)Cl>[Cl:29][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])[CH3:30])[N:17]=2)[CH:28]=[CH:27][C:24]=1[C:25]#[N:26]

Participants

4

Reactant 2

HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 86714648HCID 86714648, compound

Product 1

HCID 66576844HCID 66576844, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 1-(2-methylprop-1-en-1-yl)-1H-pyrazole-3-carboxylic acid (1.151 mmol, 191 mg) and (S)-4-(1-(2-amino-propyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (0.959 mmol, 250 mg) using DCM (5 ml) as the solvent. The mixture was diluted with DCM and washed with 1 M Na2CO3. The organic phase was dried, filtered and evaporated. The crude product was purified flash chromatography. 297 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.12 (d, 3H), 1.80 (d, 3H), 1.85 (d, 3H), 4.25-4.52 (m, 3H), 6.66 (d, 1H), 6.77-6.81 (m, 1H), 6.95 (d, 1H), 7.83 (t, 2H), 7.94-7.97 (m, 2H), 8.06-8.10 (m, 1H), 8.18 (d, 1H).

Workup

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

Sources & evidence

ORD record
ord-82d3522126d447ab80f2a118518a64ae
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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