Dimethylformamide → HCID 86714637, compound

HRID 1409352Notes

Reaction equation

HRID 1409352 reaction equation
[OH:1][C@@H:2]([CH3:13])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([OH:11])=O)[N:6]=[C:5]1[CH3:12].[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>C(Cl)Cl>[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:9]([C:7]3[N:6]=[C:5]([CH3:12])[N:4]([CH2:3][C@@H:2]([OH:1])[CH3:13])[CH:8]=3)=[O:11])[CH3:32])[N:18]=2)[CH:29]=[C:28]([F:30])[C:25]=1[C:26]#[N:27]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 86714636HCID 86714636, compound

Product 1

HCID 86714637HCID 86714637, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from (S)-1-(2-hydroxypropyl)-2-methyl-1H-imidazole-4-carboxylic acid (0.608 mmol, 112 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (0.507 mmol, 141 mg) using DMF (2 ml) as the solvent. After the reaction had stopped, DCM was added and the reaction mixture was evaporated. The residue was purified by flash chromatography. The purified product was dissolved in a mixture of MeOH/DCM and washed twice with 1M NaHCO3. The organic phase was dried, filtered and evaporated. The product was further purified by trituration from diethyl ether, filtered and dried with vacuum. 31 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.01-1.08 (m, 6H), 2.33 (s, 3H), 3.68-3.91 (m, 3H), 4.22-4.48 (m, 3H), 4.91 (d, 1H), 7.02 (d, 1H), 7.47 (s, 1H), 7.86 (d, 1H), 7.94 (d, 1H), 8.01 (s, 1H), 8.06 (d, 1H).

Workup

  1. customThe title compound was prepared
  2. customthe reaction mixture was evaporated
  3. customThe residue was purified by flash chromatography
  4. dissolutionThe purified product was dissolved in a mixture of MeOH/DCM
  5. washwashed twice with 1M NaHCO3
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe product was further purified by trituration from diethyl ether
  10. filtrationfiltered
  11. customdried with vacuum

Sources & evidence

ORD record
ord-c9a16c3dfd0740f9b26feb3f1a7f7937
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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