Ammonium Chloride → tert-Butyl 4-carbamoyl-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ylcarbamate

HRID 1775044Notes

Reaction equation

HRID 1775044 reaction equation
F[P-](F)(F)(F)(F)F.C[N+:9](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[C:25]([O:29][C:30]([NH:32][C:33]1([C:66]([OH:68])=O)[CH2:38][CH2:37][N:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]3[C:53]4[C:48](=[CH:49][N:50]=[C:51]([C:54]5[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=5)[CH:52]=4)[N:47]([CH:60]4[CH2:65][CH2:64][CH2:63][CH2:62][O:61]4)[N:46]=3)[N:40]=2)[CH2:35][CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[Cl-].[NH4+].C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:66]([C:33]1([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:34][CH2:35][N:36]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]3[C:53]4[C:48](=[CH:49][N:50]=[C:51]([C:54]5[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=5)[CH:52]=4)[N:47]([CH:60]4[CH2:65][CH2:64][CH2:63][CH2:62][O:61]4)[N:46]=3)[N:40]=2)[CH2:37][CH2:38]1)(=[O:68])[NH2:9]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712533374-(tert-Butoxycarbonylamino)-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxylic acid

Product 1

HCID 71253281tert-Butyl 4-carbamoyl-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate 45.6 mg, 0.120 mmol) was added to a mixture of 4-(tert-butoxycarbonylamino)-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxylic acid (60.0 mg, 0.100 mmol), ammonium chloride 21 mg (0.40 mmol) and N,N-Diisopropylethylamine (0.087 ml, 0.50 mmol) in 2 ml of N,N-dimethylformamide. The mixture was stirred for 18 hours and concentrated. The residue was partitioned between ethyl acetate and 1% of aqueous citric acid. The organic extracts were washed with water, 5% aqueous solution of NaHCO3, brine, dried over MgSO4 and concentrated to give tert-Butyl 4-carbamoyl-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ylcarbamate. Yield 47 mg (78%). ESI MS m/z 599.2 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and 1% of aqueous citric acid
  3. washThe organic extracts were washed with water, 5% aqueous solution of NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-49e7b8846bec4868a1d78b23b3142975
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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