Hydroxylamine → HCID 178429867, compound

HRID 2244079Notes

Reaction equation

HRID 2244079 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[C:20]4[CH2:19][C:18]([CH3:22])([CH3:21])[CH2:17][C:16](=[O:23])[C:15]=4[C:14]([CH3:24])=[CH:13]3)=[CH:9][CH:10]=2)[C:5]([C:25]#[N:26])=[CH:4][N:3]=1.[NH2:27][OH:28].C(N(CC)CC)C>CCO>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:12]3[C:20]4[CH2:19][C:18]([CH3:21])([CH3:22])[CH2:17][C:16](=[O:23])[C:15]=4[C:14]([CH3:24])=[CH:13]3)=[CH:9][CH:10]=2)[C:5]([C:25]([NH:27][OH:28])=[NH:26])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 8471TriethylamineHCID 25061240HCID 25061240, compound

Product 1

HCID 178429867HCID 178429867, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1-amino-6-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indol-1-yl)-isoquinoline-4-carbonitrile (0.035 g, 0.1 mmol), hydroxylamine (7 mg, 0.1 mmol) and triethylamine (0.01 mL, 0.1 mmol) in EtOH (2 mL) is placed in an oil bath at 100° C. and stirred for 2 days. The solvent is evaporated under reduced pressure, and the residue is purified using a Biotage column (0-20% MeOH/CH2Cl2) to afford 0.017 g (48%) of 1-amino-N-hydroxy-6-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indol-1-yl)-isoquinoline-4-carboxamidine. LC/MS m/z=378 [M+H]+, RT=1.82 min.

Workup

  1. customis placed in an oil bath at 100° C.
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is purified

Sources & evidence

ORD record
ord-d14ff28330fe4bd3ad299dd844cda953
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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