Ethanolamine → HCID 59242122, compound

HRID 1876169Notes

Reaction equation

HRID 1876169 reaction equation
Cl[C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:22][CH3:23])[CH:8]=2)[N:3]=1.[OH:24][CH2:25][CH2:26][NH2:27]>>[CH3:23][O:22][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:27][CH2:26][CH2:25][OH:24])[N:11]=[C:10]2[N:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:13]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 59242113HCID 59242113, compound

Product 1

HCID 59242122HCID 59242122, compound

Procedure

A mixture of (2-chloro-6-methoxy-quinazoline-4-yl)-(4-methoxy-phenyl)-methyl-amine (0.2 g, 0.60 mmol), and 2-hydroxylethylamine (1.5ml) was microwaved at 120° C. for 20 min. The excess of 2-hydroxylamine evaporated under reduced pressure. The product was isolated by preparative TLC (CH2CL2/MeOH=5/3 as eluent) yielded 35 mg (18%). 1H NMR (DMSO): δ 7.2 (d, 2H), 7.1 (d, 2H), 7.05 (d, 1H), 6.9 (d, 2H), 6.2 (s, 1H), 3.75 (s, 3H), 3.5 (t, 2H), 3.4 (t, 2H), 3.41 (s, 3H), 3.2 (s, 3H).

Workup

  1. customwas microwaved at 120° C. for 20 min
  2. customThe excess of 2-hydroxylamine evaporated under reduced pressure
  3. customThe product was isolated by preparative TLC (CH2CL2/MeOH=5/3 as eluent)
  4. customyielded 35 mg (18%)

Sources & evidence

ORD record
ord-355cc3291de947ac8d2eb3933b322467
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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