Ethanolamine → HCID 59239426, compound

HRID 1697987Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[C:11]3[CH2:17][CH2:16][N:15]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:14][C:12]=3[N:13]=2)=[CH:4][CH:3]=1.O1CCOCC1.C(N(CC)CC)C.[C:42](Cl)(Cl)=[O:43].[CH2:46]([CH2:48][NH2:49])[OH:47]>C1(C)C=CC=CC=1>[OH:47][CH2:46][CH2:48][NH:49][C:42]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][C@@H:23]3[CH3:28])[C:11]3[CH2:17][CH2:16][N:15]([C:18](=[O:21])[CH2:19][CH3:20])[CH2:14][C:12]=3[N:13]=2)=[CH:6][CH:7]=1)=[O:43]

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-1-(2-(4-aminophenyl)-4-(3-methylmorpholino)-5,6-dihydropyrido[3,4-d]pyrimidin-7(8H)-yl)propan-1-one (0.100 g, 0.000262 mol) in dry 1,4-Dioxane (2.00 mL, 0.0256 mol) was added Triethylamine (0.0402 mL, 0.000288 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.150 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added Ethanolamine (0.0950 mL, 0.00157 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (500 MHz, DMSO) δ 8.80 (s, 1H), 8.18 (d, J=8.7, 2H), 7.48 (d, J=8.6, 2H), 6.29 (s, 1H), 4.75-4.55 (m, 2H), 4.47 (d, J=18.2, 1H), 4.11 (s, 1H), 3.87 (d, J=12.4, 1H), 3.70 (d, J=11.5, 2H), 3.61 (d, J=11.7, 3H), 3.44 (d, J=16.7, 3H), 3.17 (dd, J=11.3, 5.7, 2H), 2.73 (s, 1H), 2.62 (s, 1H), 2.45 (dd, J=14.7, 7.6, 2H), 1.26 (d, J=6.2, 3H), 1.04 (dd, J=15.4, 7.6, 3H). LC/MS-m/z+469.3 (M+H)+

Workup

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

Sources & evidence

ORD record: ord-f669c6808d3b4a56bb37bec719050a24
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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