Ethanolamine → HCID 59239518, compound

HRID 1697983Notes

Reaction equation

HRID 1697983 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]3[CH3:26])[C:11]3[CH2:17][CH2:16][N:15]([CH:18]=[O:19])[CH2:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[O:27]1CCOC[CH2:28]1.C(N(CC)CC)C.C(Cl)(Cl)=O.[CH2:44]([CH2:46][NH2:47])[OH:45]>C1(C)C=CC=CC=1>[CH:18]([N:15]1[CH2:16][CH2:17][C:11]2[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C@@H:21]3[CH3:26])=[N:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:28]([NH:47][CH2:46][CH2:44][OH:45])=[O:27])=[CH:7][CH:6]=3)=[N:13][C:12]=2[CH2:14]1)=[O:19]

Participants

7

Reactant 5

HCID 700EthanolamineHCID 6371PhosgeneHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 86640111HCID 86640111, compound

Product 1

HCID 59239518HCID 59239518, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

(S)-2-(4-aminophenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carbaldehyde (0.100 g, 0.000283 mol) in dry 1,4-Dioxane (2.00 mL, 0.0256 mol) was added Triethylamine (0.0434 mL, 0.000311 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.170 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added ethanolamine (0.1020 mL, 0.001690 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. LC/MS-m/z+441.2 (M+H)+

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-da7996b017964ad2912ff16da4ba3765
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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