Dimethylformamide → HCID 86714634, compound

HRID 1409346Notes

Reaction equation

HRID 1409346 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([N:7]2[CH:11]=[CH:10][C:9]([C:12]([OH:14])=O)=[N:8]2)[CH:4]=[N:3]1.[NH2:15][C@@H:16]([CH3:33])[CH2:17][N:18]1[CH:22]=[CH:21][C:20]([C:23]2[CH:30]=[C:29]([F:31])[C:26]([C:27]#[N:28])=[C:25]([Cl:32])[CH:24]=2)=[N:19]1.CN(C=O)C>C(Cl)Cl>[Cl:32][C:25]1[CH:24]=[C:23]([C:20]2[CH:21]=[CH:22][N:18]([CH2:17][C@@H:16]([NH:15][C:12]([C:9]3[CH:10]=[CH:11][N:7]([C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)[N:8]=3)=[O:14])[CH3:33])[N:19]=2)[CH:30]=[C:29]([F:31])[C:26]=1[C:27]#[N:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 79779409HCID 79779409, compound

Product 1

HCID 86714634HCID 86714634, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 1′-methyl-1′H-[1,4′-bipyrazole]-3-carboxylic acid (0.861 mmol, 165 mg) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (0.718 mmol, 200 mg) and using DMF (2 ml) as the solvent. DCM was added and the reaction mixture was evaporated. The residue was purified by flash chromatography. The purified product was dissolved in DCM and washed three times with 1 M NaHCO3. The combined organics were evaporated. 134 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.15 (d, 3H), 3.88 (s, 3H), 4.28-4.42 (m, 2H), 4.42-4.52 (m, 1H), 6.75 (d, 1H), 7.01 (d, 1H), 7.81-7.88 (m, 3H), 7.94 (s, 1H), 8.13-8.17 (m, 2H), 8.18 (s, 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 DCM
  5. washwashed three times with 1 M NaHCO3
  6. customThe combined organics were evaporated

Sources & evidence

ORD record
ord-61e919e0a7034717b0e254267cd1c99a
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

Loading…