Benzylamine → HCID 86616741, compound

HRID 1678211Notes

Reaction equation

HRID 1678211 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]2[C:11]([C:12]3[CH:13]=[C:14]4[C:18](=[C:19]([C:21]([OH:23])=[O:22])[CH:20]=3)[NH:17][N:16]=[CH:15]4)=[CH:10][NH:9][C:6]2=[CH:7][N:8]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:21]([OH:23])(=[O:22])[CH3:19].[CH2:24]([NH:31][C:21]([C:19]1[CH:20]=[C:12]([C:11]2[C:5]3[C:6](=[CH:7][N:8]=[C:3]([NH2:2])[CH:4]=3)[NH:9][CH:10]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][N:16]=[CH:15]2)=[O:23])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66790891HCID 66790891, compound

Product 1

HCID 86616741HCID 86616741, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(5-amino-1H-pyrrolo[2,3-c]pyridin-3-yl)-1H-indazole-7-carboxylic acid hydrochloride (Preparation #13, 32.9 mg, 0.10 mmol) and benzylamine (24.0 μL, 0.22 mmol) in DMF (1.0 mL) were treated with o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (38.0 mg, 0.10 mmol) at ambient temperature and the reaction was stirred for about 1 hour. The reaction was concentrated under reduced pressure and the residue was purified by preparative HPLC (Waters Symmetry C8 column (25×100 mm, 7 μm particle size) using a gradient of 10%-100% CH3CN/0.1% aqueous TFA over 8 min (10 min run time) at a flow rate of 40 mL/min). Product fractions were combined and concentrated to remove organic solvents and then lyophilized to yield N-benzyl 5-(5-amino-1H-pyrrolo[2,3-c]pyridin-3-yl)-1H-indazole-7-carboxamide acetate (10 mg, 23%) as an off-white powder; RP-HPLC (Table 1, Method e) Rt 1.94 min; m/z: (M−H)− 381.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was purified by preparative HPLC (Waters Symmetry C8 column (25×100 mm, 7 μm particle size)
  3. customover 8 min
  4. custom(10 min run time)
  5. concentrationconcentrated
  6. customto remove organic solvents

Sources & evidence

ORD record
ord-296444db8b5f429da65928221d8c3dc2
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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