N-[2-[N-ethyl-N-[2-[(6-fluoropyridin-2-yl)amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide → n-[2-[n-Ethyl-n-[2-[(6-fluoropyridin-2-yl)amino]ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt
Reaction equation
[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[CH:28]=[N:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([I:29])[CH:25]=2)[N:20]=1)=[O:18])[CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[N:8]=1)[CH3:2].[ClH:30].Cl.C(N(CCNC(C1C=NC2C(=CC=C(I)C=2)N=1)=O)CCOC1C(F)=NC=CC=1)C>>[ClH:30].[ClH:30].[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[CH:28]=[N:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([I:29])[CH:25]=2)[N:20]=1)=[O:18])[CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[N:8]=1)[CH3:2]Participants
Reactant 2
Product 1
Procedure
This compound was prepared, starting from compound 16 (251 mg, 0.49 mmol), according to the procedure developed for compound 11 to give compound 17 (231 mg, 0.40 mmol) as a very hygroscopic yellow solid. Yield 80%; mp 99-101° C. (dec.); IR (KBr) ν 1163, 1225, 1421, 1474, 1522, 1622, 1670, 2500-2800, 2850-3000, 3100-3600 cm−1; 1H NMR (400 MHz, DMSO-d6) δ 1.28 (t, 3H, J=7.0 Hz), 3.33 (q, 2H, J=6.6 Hz), 3.62 (m, 2H), 3.80 (m, 6H), 6.12 (dd, 1H, J=2.0, 8.0 Hz), 6.40 (dd, 1H, J=2.0, 8.0 Hz), 7.30 (se, 1H), 7.50 (q, 1H, 4JH-F=8.0 Hz, J=8.0 Hz), 7.92 (d, 1H, J=8.8 Hz), 8.25 (dd, 1H, J=1.8, 8.8 Hz), 8.64 (d, 1H, J=1.6 Hz), 9.38 (t, 1H, J=6.0 Hz), 9.44 (s, 1H), 10.28 (se, 1H); ESI-MS m/z 509.1 [M+H]+; Anal. Calcd for C20H22OIN6F, 2HCl: C, 41.33; H, 4.16; N, 14.46. Found: C, 43.19; H, 4.31; N, 14.74.
Workup
- customThis compound was prepared
Sources & evidence
- ORD record
- ord-f03788cf4ae04ed192af78a630b8dc37
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09125937B2
Reaction notes
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