Dimethylformamide → HCID 66576765, compound

HRID 1409415Notes

Reaction equation

HRID 1409415 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]([CH3:31])[CH2:16][N:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([Cl:30])[CH:23]=2)=[N:18]1.C(Cl)Cl.CN(C=O)C>O>[Cl:30][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])[CH3:31])[N:18]=2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344Dichloromethane2×HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 86714640HCID 86714640, compound

Product 1

HCID 66576765HCID 66576765, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 5-(1-hydroxy-2-methyl-propyl)isoxazole-3-carboxylic acid (1.566 mmol, 290 mg) and (S)-4-(1-(2-amino-propyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (1.044 mmol, 272 mg) using a mixture of DCM (5 ml) and DMF (1 ml) as the solvent. DCM and water were added, the phases were separated and the water phase was extracted with DCM. The combined organics were washed twice with water. The DCM phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and preparative HPLC, respectively. 23.4 mg of the title compound was obtained. 1H-NMR (400 MHz, CDCl3): δ 0.94 (d, 3H), 0.98 (d, 3H), 1.23 (d, 3H), 2.06-2.21 (m, 1H), 4.21-4.30 (m, 1H), 4.37-4.46 (m, 1H), 4.51-4.67 (m, 2H), 6.57-6.65 (m, 2H), 7.50 (d, 1H), 7.68 (d, 1H), 7.78-7.86 (m, 1H), 7.97 (d, 1H), 8.04 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customthe phases were separated
  3. extractionthe water phase was extracted with DCM
  4. washThe combined organics were washed twice with water
  5. dry with materialThe DCM phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography and preparative HPLC

Sources & evidence

ORD record
ord-03165a53171e41089e3747dee6a83aac
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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