Ethanolamine → HCID 59239309, compound

HRID 1697985Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][C@@H:22]3[CH3:27])[C:11]3[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH3:19])[CH2:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.[O:28]1CCOC[CH2:29]1.C(N(CC)CC)C.C(Cl)(Cl)=O.[CH2:45]([CH2:47][NH2:48])[OH:46]>C1(C)C=CC=CC=1>[C:18]([N:15]1[CH2:16][CH2:17][C:11]2[C:10]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][C@@H:22]3[CH3:27])=[N:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:29]([NH:48][CH2:47][CH2:45][OH:46])=[O:28])=[CH:7][CH:6]=3)=[N:13][C:12]=2[CH2:14]1)(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-1-(2-(4-aminophenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)ethanone (0.100 g, 0.000272 mol) in dry 1,4-Dioxane (2.00 mL, 0.0256 mol) was added Triethylamine (0.0416 mL, 0.000299 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.1580 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added Ethanolamine (0.0986 mL, 0.00163 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.80 (d, J=5.5, 1H), 8.18 (dd, J=8.7, 3.1, 2H), 7.69 (s, 1H), 7.48 (d, J=8.5, 2H), 6.26 (s, 1H), 4.69-4.57 (m, 2H), 4.48 (d, J=18.7, 1H), 4.14 (s, 1H), 3.88 (d, J=9.4, 1H), 3.62 (ddd, J=22.1, 21.5, 8.2, 6H), 3.46 (t, J=5.7, 2H), 3.17 (dd, J=11.1, 5.5, 2H), 2.75 (s, 1H), 2.63 (s, 1H), 2.09 (d, J=27.2, 3H), 1.31-1.21 (m, 3H).

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationThe reaction mixture was concentrated
custompurified by HPLC

Sources & evidence

ORD record: ord-9ab9a627859f4c6a831a3faf731b6267
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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