Hydrochloric Acid → 6-Chloro-2,4,8,15,23-pentazatetracyclo[15.3.1.13,7.19,13]tricosa-1(20),3,5,7(23),9,11,13(22),17(21),18-nonaen-14-one

HRID 541814Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=2)[C:12]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([NH:22]C(=O)OC(C)(C)C)[CH:19]=[CH:20][CH:21]=2)=[O:13])[C:5]([Cl:33])=[CH:4][N:3]=1.Cl>COCCO.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[Cl:33][C:5]1[CH:4]=[N:3][C:2]2[NH:22][C:18]3[CH:19]=[CH:20][CH:21]=[C:16]([CH:17]=3)[CH2:15][NH:14][C:12](=[O:13])[C:11]3[CH:10]=[C:9]([NH:8][C:6]=1[N:7]=2)[CH:32]=[CH:31][CH:30]=3

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of tert-butyl {3-[({3-[(2,5-dichloropyrimidin-4-yl)amino]benzoyl}amino)methyl]phenyl}carbamate (40.0 mg, 0.0819 mmol) in 2-methoxyethanol (0.452 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (100 μL). The resulting mixture was heated at 150° C. in the microwave for 15 min. The cloudy mixture was diluted with Na2CO3 (aq), filtered, washed with water. The crude cake was triturated with MeOH to give the desired product as an off-white powder (18 mg, 62%). LCMS for C18H14ClN5O (M+H)+: m/z=352.0. 1H NMR (400 MHz, DMSO-d6): δ 10.24 (s, 1H), 10.05 (t, J=2.0 Hz, 1H), 9.66 (s, 1H), 9.05 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 8.62 (t, J=2.0 Hz, 1H), 8.25 (t, J=8.0 Hz, 1H), 8.00 (m, 1H), 7.76 (ddd, J=7.6, 2.0, 1.2, 1H), 7.52 (m, 1H), 7.36 (t, J=7.6 Hz, 1H), 7.02 (m, 1H), 6.90 (m, 1H), 4.32 (s, 2H).

Workup

filtrationfiltered
washwashed with water
customThe crude cake was triturated with MeOH

Sources & evidence

ORD record: ord-44711fd286e04b7d8deaf2ac638ae409
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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