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Ammonia → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide

HRID 1504854
Notes
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Reaction equation

HRID 1504854 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:10]1[CH:11]=[C:12]([NH:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=2)[C:13]([C:16]([NH2:18])=[O:17])=[N:14][CH:15]=1.N>CO.O>[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[NH:9][C:10]1[CH:11]=[C:12]([NH:19][C:20]2[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[N:21]=2)[C:13]([C:16]([NH2:18])=[O:17])=[N:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 222AmmoniaHCID 867317225-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide hydrochloric acid salt

Product 1

HCID 715336755-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962
Water
Solvent

Procedure

The 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide hydrochloric acid salt (21.5 g, 50.3 mmol) was diluted with methanol (200 mL) and ammonia (7.0 M solution in methanol, 21.6 mL, 151 mmol). After 30 minutes, the reaction mixture was diluted with water (190 mL) and stirred. After 30 minutes, the reaction mixture was filtered, and the solids were washed with water (2×75 mL) and dried to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-[(4,6-dimethylpyridin-2-yl)amino]pyridine-2-carboxamide. MS ESI calc'd. for C19H27N6O [M+H]+ 355. found 355. 1H NMR (600 MHz, CD3OD) δ 8.47 (d, J=2.4 Hz, 1H), 7.58 (d, J=2.4 Hz, 1H), 6.58 (s, 1H), 6.47 (s, 1H), 3.61-3.49 (m, 1H), 3.26-3.22 (m, 1H), 2.39 (s, 3H), 2.23 (s, 3H), 1.87-1.55 (m, 6H), 1.49-1.39 (m, 2H).

Workup

  1. waitAfter 30 minutes
  2. filtrationthe reaction mixture was filtered
  3. washthe solids were washed with water (2×75 mL)
  4. customdried

Sources & evidence

ORD record
ord-e27b60cbf0c7452e817794e7b9a9924a
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09216173B2

Reaction notes

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