3-Aminopropionitrile → HCID 59239379, compound

HRID 1697991Notes

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.[O:31]1[CH2:36]COCC1.C(N(CC)CC)C.C(Cl)(Cl)=O.[C:48]([CH2:50][CH2:51][NH2:52])#[N:49]>C1(C)C=CC=CC=1>[C:48]([CH2:50][CH2:51][NH:52][C:36]([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:31])#[N:49]

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 β-Cyanoethylamine (0.0764 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 8.94 (s, 1H), 8.56 (s, 1H), 8.22 (d, J=8.8, 2H), 8.17 (s, 1H), 7.52 (d, J=8.8, 2H), 6.96 (d, J=5.5, 1H), 6.58 (t, J=5.9, 1H), 4.76 (d, J=18.3, 1H), 4.65 (d, J=18.0, 1H), 4.13 (d, J=6.6, 1H), 3.99 (s, 1H), 3.88 (d, J=11.3, 1H), 3.81-3.55 (m, 7H), 3.46-3.32 (m, 1H), 2.74 (d, J=10.3, 2H), 2.70 (t, J=6.4, 2H), 1.26 (d, J=6.6, 3H). LC/MS-m/z+500.3 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-36e8844e3efd4e7f922c66089e8baf86
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163763B2

Reaction notes

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