Ethanolamine → HCID 51035659, compound

HRID 2039544Notes

Reaction equation

HRID 2039544 reaction equation
[NH2:1][C:2]1[N:14]=[C:13]2[N:4]([C:5]([CH2:18][C:19]3[CH:27]=[CH:26][C:22]4[O:23][CH2:24][O:25][C:21]=4[CH:20]=3)=[N:6][C:7]3[CH:8]=[C:9]([C:15](O)=[O:16])[CH:10]=[CH:11][C:12]=32)[N:3]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:59][CH2:60][CH2:61][OH:62]>ClCCl>[OH:62][CH2:61][CH2:60][NH:59][C:15]([C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:4]([N:3]=[C:2]([NH2:1])[N:14]=3)[C:5]([CH2:18][C:19]3[CH:27]=[CH:26][C:22]4[O:23][CH2:24][O:25][C:21]=4[CH:20]=3)=[N:6][C:7]=2[CH:8]=1)=[O:16]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67042898HCID 67042898, compound

Product 1

HCID 51035659HCID 51035659, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-5-benzo[1,3]dioxol-5-ylmethyl-[1,2,4]triazolo[1,5-c]quinazoline-8-carboxylic acid (0.05 g, 0.14 mmol) prepared as described in Example 19, and N,N-diisopropylethylamine (0.14 mL, 0.81 mmol) in anhydrous dichloromethane (5 mL), TBTU (0.05 g, 0.17 mmol) was added. The reaction was stirred at room temperature for 30 minutes, then 2-aminoethanol (0.02 mL, 0.28 mmol) was added. After stirring for 1 h, the solution washed with NaHCO3 satured solution, then with water and brine. The organic phase was dried over Na2SO4 and evaporated to give a crude that was purified by flash column chromatography on silica gel eluting with DCM/MeOH/NH4OH 8/2/1, to provide the title compound (0.03 g, 53% yield).

Workup

  1. additionwas added
  2. stirringAfter stirring for 1 h
  3. washthe solution washed with NaHCO3 satured solution
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated
  6. customto give a crude that
  7. customwas purified by flash column chromatography on silica gel eluting with DCM/MeOH/NH4OH 8/2/1

Sources & evidence

ORD record
ord-69e04e1afde943c781bccc4e4be4903b
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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