Hydrochloric Acid → (R)-2-(aminomethyl)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-imidazole-5-carboxamide

HRID 872604Notes

Reaction equation

HRID 872604 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@H:16]([NH:18][C:19]([C:21]3[NH:25][C:24]([CH2:26][NH:27]C(=O)OC(C)(C)C)=[N:23][CH:22]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].Cl>CCO>[NH2:27][CH2:26][C:24]1[NH:25][C:21]([C:19]([NH:18][C@H:16]([CH3:17])[CH2:15][N:12]2[CH:13]=[CH:14][C:10]([C:4]3[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[CH:3]=3)=[N:11]2)=[O:20])=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86670244HCID 86670244, compound

Product 1

HCID 70655528(R)-2-(aminomethyl)-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-imidazole-5-carboxamideYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-tert-butyl (5-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamoyl)-1H-imidazol-2-yl)methylcarbamate (0.42 mmol) was stirred with 10% HCl (g) in EtOH (30 ml) overnight. Solvent was evaporated and the residue was taken up in water (50 ml), washed with DCM (3×30 ml) and made strongly alkaline by adding 2 M NaOH solution. The water phase was extracted with DCM (3×50 ml) and combined organic phases were dried over Na2SO4 and evaporated to yield 104 mg (65%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 1.08 (d, 3H), 3.73 (s, 2H), 4.27 (dd, 1H), 4.32-4.48 (m, 2H), 6.95 (d, 1H), 7.44 (s, 1H), 7.83 (d, 1H), 7.94-8.03 (m, 2H), 8.07 (d, 1H), 8.10 (m, 1H).

Workup

  1. customSolvent was evaporated
  2. washwashed with DCM (3×30 ml)
  3. additionby adding 2 M NaOH solution
  4. extractionThe water phase was extracted with DCM (3×50 ml)
  5. dry with materialwere dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-c6830d629f264171b02752bcc09477cf
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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