O-[2-(Morpholin-4-yl)ethyl]hydroxylamine → HCID 178433354, compound

HRID 1917499Notes

Reaction equation

HRID 1917499 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][NH2:10])[CH2:3][CH2:2]1.[NH2:11][C:12]1[N:13]=[C:14]([CH3:31])[C:15]2[C:21](=S)[NH:20][C@@H:19]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[Br:30])[CH2:18][C:16]=2[N:17]=1>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9]/[N:10]=[C:21]2\[NH:20][C@@H:19]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[Br:30])[CH2:18][C:16]3[N:17]=[C:12]([NH2:11])[N:13]=[C:14]([CH3:31])[C:15]\2=3)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 13127327O-[2-(Morpholin-4-yl)ethyl]hydroxylamineHCID 45257321HCID 45257321, compound

Product 1

HCID 178433354HCID 178433354, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of O-(2-morpholinoethyl)hydroxylamine (600 mg, 4.1 mmol) in anhydrous toluene (6 mL) was added (R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-5(6H)-thione (0.150 g, 0.41 mmol) and mercuric acetate (II) (262 mg, 0.82 mmol). The resultant mixture was heated to 100° C. for 1 h. The reaction was allowed to cool to r.t. and filtered through a pad of Celite, rinsing with EtOAc and CH3OH. The filtrate was concentrated to provide a yellow-green oil, which was purified by preparative HPLC eluting with TFA/ACN/H2O. The fractions were concentrated to provide (R,Z)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one O-2-morpholinoethyl oxime (196 mg, 0.41 mmol). [M+H] calc'd for C20H24BrFN6O2, 480; found, 480.

Workup

  1. filtrationfiltered through a pad of Celite
  2. washrinsing with EtOAc and CH3OH
  3. concentrationThe filtrate was concentrated
  4. customto provide a yellow-green oil, which
  5. customwas purified by preparative HPLC
  6. washeluting with TFA/ACN/H2O
  7. concentrationThe fractions were concentrated

Sources & evidence

ORD record
ord-65a36a3288b24b14b77c35c79352d796
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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