HCID 11062693, compound → HCID 70656906, compound

HRID 872684Notes

Reaction equation

HRID 872684 reaction equation
[Cl:1][CH2:2][C:3]1[O:4][CH:5]=[C:6]([C:8]([OH:10])=O)[N:7]=1.[NH2:11][C@@H:12]([CH3:28])[CH2:13][N:14]1[CH:18]=[CH:17][C:16]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[CH:20]=2)=[N:15]1>C(Cl)Cl>[Cl:27][C:21]1[CH:20]=[C:19]([C:16]2[CH:17]=[CH:18][N:14]([CH2:13][C@@H:12]([NH:11][C:8]([C:6]3[N:7]=[C:3]([CH2:2][Cl:1])[O:4][CH:5]=3)=[O:10])[CH3:28])[N:15]=2)[CH:26]=[CH:25][C:22]=1[C:23]#[N:24]

Participants

4

Reactant 2

HCID 11062693HCID 11062693, compoundHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656906HCID 70656906, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-(chloromethyl)oxazole-4-carboxylic acid (400 mg, 2.476 mmol) and 1,3-DCC (5110 mg, 2.476 mmol) were dissolved in dry DCM and stirred for 30 min. (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (646 mg, 2.476 mmol) in dry DCM was added to the reaction mixture and stirred at RT overnight. The reaction mixture was diluted with DCM and washed twice with water. Organic phase was evaporated to dryness and the product was purified with Flash-chromatography. Yield 36.9%. m/z [404.3+1].

Workup

  1. additionwas added to the reaction mixture
  2. washwashed twice with water
  3. customOrganic phase was evaporated to dryness
  4. customthe product was purified with Flash-chromatography

Sources & evidence

ORD record
ord-57132305135e42608eda68135d450922
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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