1-Hydroxybenzotriazole → HCID 70656318, compound

HRID 872582Notes

Reaction equation

HRID 872582 reaction equation
[O:1]1[N:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[N:2]1.C1C=CC2N(O)N=NC=2C=1.N=C=N.[NH2:22][C@@H:23]([CH3:39])[CH2:24][N:25]1[CH:29]=[CH:28][C:27]([C:30]2[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[C:32]([Cl:38])[CH:31]=2)=[N:26]1>C(Cl)Cl>[Cl:38][C:32]1[CH:31]=[C:30]([C:27]2[CH:28]=[CH:29][N:25]([CH2:24][C@@H:23]([NH:22][C:6]([C:3]3[CH:4]=[N:5][O:1][N:2]=3)=[O:8])[CH3:39])[N:26]=2)[CH:37]=[CH:36][C:33]=1[C:34]#[N:35]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 160435CarbodiimideHCID 14155241,2,5-oxadiazole-3-carboxylic acidHCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile

Product 1

HCID 70656318HCID 70656318, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,2,5-oxadiazole-3-carboxylic acid (66 mg, 0.58 mmol) in 5 ml of DCM were added anhydrous HOBt (88 mg, 0.65 mmol) and PS-carbodiimide (590 mg, 0.77 mmol). After 10 min (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (100 mg, 0.38 mmol) was added and the reaction mixture was stirred at RT overnight. Resin was filtered and washed twice with DCM. Filtrate was washed with 10% citric acid, 1 M NaHCO3-solution, brine and water. Organic phase was dried over Na2SO4, filtered and evaporated to give 111 mg (81%) of the title compound. 1H-NMR (400 MHz; CDCl3): δ 1.25 (d, 3H), 4.25 (dd, 1H), 4.48 (dd, 1H), 4.58-4.70 (m, 1H), 6.66 (d, 1H), 7.51 (d, 1H), 7.71 (dd, 1H), 7.83 (dd, 1H), 8.01 (dd, 1H), 8.31 (d, 1H), 8.65 (s, 1H).

Workup

  1. filtrationResin was filtered
  2. washwashed twice with DCM
  3. washFiltrate was washed with 10% citric acid, 1 M NaHCO3-solution, brine and water
  4. dry with materialOrganic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b1a393e3c79b4e8f8cb1d4f7c868cb7b
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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