Dicyclohexylcarbodiimide → HCID 67172292, compound

HRID 872725Notes

Reaction equation

HRID 872725 reaction equation
[Br:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([OH:10])=O)[CH:4]=1.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:26][C@@H:27]([CH3:43])[CH2:28][N:29]1[CH:33]=[CH:32][C:31]([C:34]2[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[C:36]([Cl:42])[CH:35]=2)=[N:30]1>C(Cl)Cl>[Br:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([NH:26][C@@H:27]([CH3:43])[CH2:28][N:29]2[CH:33]=[CH:32][C:31]([C:34]3[CH:41]=[CH:40][C:37]([C:38]#[N:39])=[C:36]([Cl:42])[CH:35]=3)=[N:30]2)=[O:10])[CH:4]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 133710205-(Bromomethyl)-1,2-oxazole-3-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 67172292HCID 67172292, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Bromomethyl)isoxazole-3-carboxylic acid (1.027 g, 4.99 mmol) and DCC (1.029 g, 4.99 mmol) were dissolved in dry DCM under nitrogen atmosphere and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (1.0 g, 3.84 mmol) was added. The mixture was stirred overnight at RT and a precipitate was filtered. The filtrate was washed with water, dried and evaporated to dryness. The evaporation residue was purified by Flash-chromatography to give the title compound. Yield 83%. 1H-NMR (400 MHz; DMSO): δ 1.17 (d, 3H), 4.32 (d, 2H), 4.40-4.50 (m, 1H), 4.86 (s, 2H), 6.81 (s, 1H), 6.94 (d, 1H), 7.82 (d, 1H), 7.91 (dd, 1H), 7.97 (dd, 1H), 8.08 (dd, 1H). 8.85 (d, 1H)

Workup

  1. filtrationa precipitate was filtered
  2. washThe filtrate was washed with water
  3. customdried
  4. customevaporated to dryness
  5. customThe evaporation residue was purified by Flash-chromatography

Sources & evidence

ORD record
ord-6c054c9b7b66478189a436db63a12ada
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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