Ethanolamine → HCID 59239236, compound

HRID 1697990Notes

Reaction equation

[CH3:1][C@@H:2]1[N:7]([C:8]2[C:9]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][N:26]=4)[CH2:21][C:10]=3[N:11]=[C:12]([C:14]3[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=3)[N:13]=2)[CH2:6][CH2:5][O:4][CH2:3]1.O1CCOCC1.C(N(CC)CC)C.[C:44](Cl)(Cl)=[O:45].[CH2:48]([CH2:50][NH2:51])[OH:49]>C1(C)C=CC=CC=1>[OH:49][CH2:48][CH2:50][NH:51][C:44]([NH:18][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[N:13]=[C:8]([N:7]3[CH2:6][CH2:5][O:4][CH2:3][C@@H:2]3[CH3:1])[C:9]3[CH2:24][CH2:23][N:22]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][N:26]=4)[CH2:21][C:10]=3[N:11]=2)=[CH:20][CH:19]=1)=[O:45]

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-4-(4-(3-methylmorpholino)-7-(pyrimidin-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)aniline (0.0700 g, 0.000173 mol) in dry 1,4-Dioxane (1.50 mL, 0.0192 mol) was added Triethylamine (0.0266 mL, 0.000191 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.100 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added Ethanolamine (0.0628 mL, 0.00104 mol). The reaction mixture was stirred overnight. The reaction mixture was concentrated and purified by HPLC. 1H NMR (400 MHz, DMSO) δ 8.82 (s, 1H), 8.56 (s, 1H), 8.22 (dd, J=13.0, 7.3, 3H), 7.49 (d, J=8.8, 2H), 6.96 (d, J=5.4, 1H), 6.30 (t, J=5.6, 1H), 4.76 (d, J=18.6, 1H), 4.64 (d, J=18.3, 1H), 4.13 (d, J=6.9, 1H), 4.01 (d, J=12.8, 1H), 3.88 (d, J=11.5, 1H), 3.80-3.57 (m, 5H), 3.45 (m, 3H), 3.17 (m, 2H), 2.75 (s, 2H), 1.26 (d, J=6.7, 3H). LC/MS-m/z+491.2 (M+H)+

Workup

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

Sources & evidence

ORD record: ord-2ac217f74dc947249c0e65410b61df81
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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