Hydroxyamine hydrochloride → HCID 66640723, compound

HRID 1615952Notes

Reaction equation

HRID 1615952 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:20][NH:21][C:22]1[C:27]([CH3:28])=[C:26]([N:29]2[CH2:34][CH2:33][CH:32]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([N:41]4C(C)=CC=C4C)[N:36]=3)[CH2:31][CH2:30]2)[N:25]=[CH:24][N:23]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO>C(O)C.O>[NH2:41][C:37]1[N:36]=[C:35]([CH:32]2[CH2:31][CH2:30][N:29]([C:26]3[N:25]=[CH:24][N:23]=[C:22]([NH:21][CH2:20][CH:12]([NH:11][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:27]=3[CH3:28])[CH2:34][CH2:33]2)[CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66641328HCID 66641328, compound

Product 1

HCID 66640723HCID 66640723, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

100 mg (0.15 mmol) of tert-butyl 2-benzyloxycarbonylamino-3-{6-[6-(2,5-dimethyl-pyrrol-1-yl)-3′,4′,5′,6′-tetrahydro-2′H-[2.4′]bipyridinyl-1′-yl]-5-methyl-pyrimidin-4-ylamino}-propionate is dissolved in 3 ml of ethanol and 0.3 ml of water. 50 mg (0.75 mmol) of hydroxylamine hydrochloride is added and the reaction medium is heated for 18 hours at 90° C. The solvents are evaporated off under reduced pressure (2 kPa) and the crude residue is purified by chromatography on silica gel eluting with a CH2Cl2/MeOH mixture 90:10. 30 mg of expected product is obtained in the form of a resin.

Workup

  1. customThe solvents are evaporated off under reduced pressure (2 kPa)
  2. customthe crude residue is purified by chromatography on silica gel eluting with a CH2Cl2/MeOH mixture 90:10

Sources & evidence

ORD record
ord-624b75d312b442648e7d2a0c74d84b62
Source dataset
uspto-grants-2014_07
Patent number
US08765766B2

Reaction notes

Loading…