Dimethylformamide → HCID 178461759, compound

HRID 1409383Notes

Reaction equation

HRID 1409383 reaction equation
[Br:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.[NH2:10][C@@H:11]([CH3:28])[CH2:12][N:13]1[CH:17]=[CH:16][C:15]([C:18]2[CH:25]=[C:24]([F:26])[C:21]([C:22]#[N:23])=[C:20]([Cl:27])[CH:19]=2)=[N:14]1.CN(C=O)C.C(Cl)Cl>O>[Br:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([NH:10][C@@H:11]([CH3:28])[CH2:12][N:13]2[CH:17]=[CH:16][C:15]([C:18]3[CH:25]=[C:24]([F:26])[C:21]([C:22]#[N:23])=[C:20]([Cl:27])[CH:19]=3)=[N:14]2)=[O:9])[N:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 67170587(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrileHCID 178524790HCID 178524790, compound

Product 1

HCID 178461759HCID 178461759, compoundYield 1.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared using the procedure described in Example 3(h) starting from 2-bromo-1H-imidazole-4-carboxylic acid (4.31 mmol, 0.822 g) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chloro-6-fluorobenzonitrile (3.59 mmol, 1 g) using DMF (10 ml) as the solvent. DCM and water was added to the mixture, the layers were separated and the water phase was extracted with DCM. The combined organics were washed three times with water. The DCM phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and preparative HPLC, respectively. 30.5 mg of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.10 (d, 3H), 4.24-4.49 (m, 3H), 7.00 (d, 1H), 7.62 (s, 1H), 7.83 (d, 1H), 7.87 (d, 1H), 7.96 (s, 1H), 8.11 (d, 1H), 13.23 (bs, 1H).

Workup

  1. customThe title compound was prepared
  2. customthe layers were separated
  3. extractionthe water phase was extracted with DCM
  4. washThe combined organics were washed three times 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-8c0e98f2204e410e8d8f559bbeea7ae0
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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