Hydroxyamine hydrochloride → HCID 178434342, compound

HRID 1038847Notes

Reaction equation

HRID 1038847 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]3[N:13]=[C:14]([N:21]4[CH2:26][CH2:25][CH:24]([C:27]#[N:28])[CH2:23][CH2:22]4)[C:15]4[O:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:8][CH:9]=2)[NH:4][N:3]=1.Cl.[NH2:30][OH:31].C([O-])(O)=O.[Na+]>CO>[OH:31][N:30]=[C:27]([CH:24]1[CH2:25][CH2:26][N:21]([C:14]2[C:15]3[O:20][CH:19]=[CH:18][C:16]=3[N:17]=[C:12]([NH:11][C:7]3[CH:6]=[C:5]4[C:10]([C:2]([CH3:1])=[N:3][NH:4]4)=[CH:9][CH:8]=3)[N:13]=2)[CH2:22][CH2:23]1)[NH2:28]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 178434341HCID 178434341, compound

Product 1

HCID 178434342HCID 178434342, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(2-(3-methyl-1H-indazol-6-ylamino)furo[3,2-d]pyrimidin-4-yl)piperidine-4-carbonitrile (0.082 g, 0.22 mmol), hydroxylamine hydrochloride (0.061 g, 0.88 mmol) and NaHCO3 (0.15 g, 1.7 mmol) in MeOH (20 mL) was stirred at about 70° C. for about 120 h. The solvent was removed and the residue was purified by preparative HPLC (Table 2, Method p) to give N′-hydroxy-1-(2-(3-methyl-1H-indazol-6-ylamino)furo[3,2-d]pyrimidin-4-yl)piperidine-4-carboximidamide (0.020 g, 22%): LC/MS (Table 2, Method h) Rt=1.66 min; MS m/z: 407 (M+H)+. Syk IC50=B

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative HPLC (Table 2, Method p)

Sources & evidence

ORD record
ord-9b400d1b3365474281d489411cb70bdf
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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