Phosgene → HCID 86640110, compound

HRID 1697982Notes

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[N:30]=[CH:29][CH: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.[O:31]1[CH2:36]COCC1.C(N(CC)CC)C.C(Cl)(Cl)=O.[F:48][CH2:49][CH2:50][NH2:51]>C1(C)C=CC=CC=1>[F:48][CH2:49][CH2:50][NH:51][C:36]([NH:18][C:17]1[CH:19]=[CH:20][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[N:26]=[CH:27][CH:28]=[CH:29][N:30]=4)[CH2:21][C:10]=3[N:11]=2)=[CH:15][CH:16]=1)=[O:31]

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-4-(4-(3-methylmorpholino)-7-(pyrimidin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)aniline (0.0501 g, 0.000124 mol) in dry 1,4-Dioxane (2.00 mL, 0.0256 mol) was added Triethylamine (0.0190 mL, 0.000136 mol) followed by 20% Phosgene in toluene (1:4, Phosgene:Toluene, 0.080 mL). The reaction mixture was heated at 50° C. for 1 hour. The reaction mixture was cooled to room temperature and then added 2-fluoroethanamine (0.0534 g, 0.000762 mol) followed by Triethylamine (0.1140 mL, 0.0008179 mol). The reaction mixture was stirred for 3 days. The reaction mixture was concentrated and purified by HPLC. LC/MS-m/z+493.2 (M+H)+

Workup

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

Sources & evidence

ORD record: ord-96060be1474b4e3a851d8c8ef3b42429
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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