2-[(S)-1-Phenylethylamino]-4-[6-azidobenzimidazol-1-yl]pyrimidine → 2-[(S)-1-Phenylethylamino]-4-[6-(4-ethoxycarbonyltriazol-1-yl)benzimidazol-1-yl]pyrimidine

HRID 2300816Notes

Reaction equation

HRID 2300816 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([N:25]=[N+:26]=[N-:27])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:28]([O:30][C:31](=[O:38])[CH:32]=[C:33](NC)NC)[CH3:29]>O1CCOCC1>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([N:25]5[CH:33]=[C:32]([C:31]([O:30][CH2:28][CH3:29])=[O:38])[N:27]=[N:26]5)[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 599246882-[(S)-1-Phenylethylamino]-4-[6-azidobenzimidazol-1-yl]pyrimidineHCID 85819813Ethyl 3,3-dimethylaminoacrylate

Product 1

HCID 599248302-[(S)-1-Phenylethylamino]-4-[6-(4-ethoxycarbonyltriazol-1-yl)benzimidazol-1-yl]pyrimidine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared from 266 mg of 2-[(S)-1-phenylethylamino]-4-[6-azidobenzimidazol-1-yl]pyrimidine, about 100 μL ethyl-3,3-dimethylaminoacrylate and 5 mL 1,4-dioxane using the procedure described in EXAMPLE 276 to give 283 mg of the title compound. RF: 0.4 (5% MeOH in CH2Cl2). 1H NMR (500 MHZ, DMSO): δ 1.33 (t, J=7.0 Hz, 3H), 1.50 (d, J=6.9 Hz, 3H), 4.38 (q, J=7.1 Hz, 2H), 5.24 (m, 1H), 7.05-7.45 (m, 5H), 7.87 (d, J=8.6 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H), 8.2 (m, 1H), 8.44 (m, 1H), 8.91 (m, 1H), 9.14 (br s, 1H), 9.50 (s, 1H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 455.2 (M+1).

Sources & evidence

ORD record
ord-8c82adef6d234d94bcc0220780a81598
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

Loading…