Hydrochloric Acid → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide hydrochloric acid salt

HRID 1504853Notes

Reaction equation

HRID 1504853 reaction equation
[C:1]([C:4]1[N:9]=[CH:8][C:7]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17]C(=O)OC(C)(C)C)=[CH:6][C:5]=1[NH:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[N:27]=1)(=[O:3])[NH2:2].[ClH:34]>O1CCOCC1>[ClH:34].[NH2:17][C@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[NH:10][C:7]1[CH:6]=[C:5]([NH:25][C:26]2[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[N:27]=2)[C:4]([C:1]([NH2:2])=[O:3])=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 86731721tert-Butyl [(1S,2R)-2-({6-carbamoyl-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl]amino)cyclohexyl}carbamate

Product 1

HCID 867317225-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide hydrochloric acid salt

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl [(1S,2R)-2-({6-carbamoyl-5-[(4,6-dimethylpyridin-2-yl)amino]pyridin-3-yl]amino)cyclohexyl}carbamate (22.5 g, 49.5 mmol) was diluted with dioxane (140 mL). To this solution was added hydrochloric acid (4.0 M in dioxane, 62 mL, 250 mmol). After 30 minutes, the reaction mixture was diluted with hexanes (400 mL) and filtered. The collected solids were dried in a nitrogen bag. The solids were diluted with dioxane (140 mL) followed by hydrochloric acid (4.0 M in dioxane, 62 mL, 250 mmol). After 1 hour, the reaction mixture was diluted with hexanes (400 mL), filtered, and washed with hexanes (2×150 mL). The isolated solids were dried under reduced pressure, and then suspended in dichloromethane (300 mL). After stirring for 3 hours, the mixture was filtered and dried in a nitrogen bag to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide hydrochloric acid salt.

Workup

  1. filtrationfiltered
  2. customThe collected solids were dried in a nitrogen bag
  3. additionThe solids were diluted with dioxane (140 mL)
  4. waitAfter 1 hour
  5. filtrationfiltered
  6. washwashed with hexanes (2×150 mL)
  7. customThe isolated solids were dried under reduced pressure
  8. filtrationthe mixture was filtered
  9. customdried in a nitrogen bag

Sources & evidence

ORD record
ord-3f3b2f90f42e453db352a04a876a061a
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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