1,4-Dioxane hydrochloride → 6-((1R,2S)-2-Aminocyclohexylamino)-7-bromo-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 2092860Notes

Reaction equation

HRID 2092860 reaction equation
[Br:1][C:2]1[C:3]2[CH2:31][NH:30][C:29](=[O:32])[C:4]=2[C:5]([C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15]C(=O)OC(C)(C)C.[ClH:33].O1CCOCC1>>[ClH:33].[NH2:15][C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]1[NH:8][C:7]1[N:6]=[C:5]([C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)[C:4]2[C:29](=[O:32])[NH:30][CH2:31][C:3]=2[C:2]=1[Br:1]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86654737tert-Butyl (1S,2R)-2-(7-bromo-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

Product 2

HCID 313Hydrochloric AcidHCID 583176056-((1R,2S)-2-Aminocyclohexylamino)-7-bromo-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneYield 22.2%

Procedure

A solution of tert-butyl (1S,2R)-2-(7-bromo-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (10 mg, 0.020 mmol) in HCl-dioxane(999 μL, 4.00 mmol) was stirred at RT for 2 h. The mixture was concentrated to a residue, diluted with Et2O (3 mL), and sonicated to yield a white precipitate, which was filtered and dried overnight in a lyophilizer to give an HCl salt of the title compound as a white solid (1.8 mg, 21%). [M+H] calc'd for C17H21BrN6O, 406. found, 406.

Workup

  1. concentrationThe mixture was concentrated to a residue
  2. additiondiluted with Et2O (3 mL)
  3. customsonicated
  4. customto yield a white precipitate, which
  5. filtrationwas filtered
  6. customdried overnight in a lyophilizer

Sources & evidence

ORD record
ord-b36006bfd5e2409aa8af84d4ccb26ddf
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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