Dimethylformamide → HCID 66576209, compound

HRID 1409341Notes

Reaction equation

HRID 1409341 reaction equation
[F:1][CH:2]([F: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.C1C=CC2N(O)N=NC=2C=1.CN(C=O)C>O>[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][CH:2]([F:1])[F: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

6

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 86714630HCID 86714630, compound

Product 1

HCID 66576209HCID 66576209, compoundYield 5.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) using 1-(2,2-difluoro-ethyl)-2-methyl-1H-imidazole-4-carboxylic acid (0.926 mmol, 176 mg), (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzo-nitrile (0.617 mmol, 172 mg) and only a catalytic amount of HOBt (0.062 mmol, 8.34 mg). DMF was used as the solvent. Water was added to the reaction mixture and the mixture was extracted it three times with DCM. The combined organics were washed twice with water. The organic phase was evaporated and the residue was purified by flash chromatography and preparative HPLC, respectively. 15.5 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.07 (d, 3H), 2.36 (s, 3H), 4.23-4.55 (m, 5H), 6.19-6.51 (m, 1H), 7.02 (d, 1H), 7.53 (s, 1H), 7.86 (d, 1H), 7.90-7.95 (m, 1H), 8.00 (s, 1H), 8.12 (d, 1H).

Workup

  1. customThe title compound was prepared
  2. extractionthe mixture was extracted it three times with DCM
  3. washThe combined organics were washed twice with water
  4. customThe organic phase was evaporated
  5. customthe residue was purified by flash chromatography and preparative HPLC

Sources & evidence

ORD record
ord-4f7806831f4e4b89b6a28a65a653327d
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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