N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodonaphthalene-2-carboxamide → N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodonaphthalene-2-carboxamide hydrochloride salt

HRID 2273648Notes

Reaction equation

HRID 2273648 reaction equation
[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([I:29])[CH:25]=2)[CH:20]=1)=[O:18])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=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].[CH2:1]([N:3]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([I:29])[CH:25]=2)[CH:20]=1)=[O:18])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

3

Reactant 2

HCID 52952163N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodonaphthalene-2-carboxamideHCID 52952259n-[2-[n-Ethyl-n-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride salt

Product 1

HCID 52952371N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]-6-iodonaphthalene-2-carboxamide hydrochloride saltYield 77%

Procedure

This compound was prepared, starting from compound 70 (150 mg, 0.30 mmol), according to the procedure developed for compound 11. Reaction time at room temperature: 12 h to give compound 71 (127 mg, 0.23 mmol) as a very hygroscopic beige solid. Yield 77%; mp 157-159° C.; IR (KBr) ν 1124, 1186, 1241, 1312, 1457, 1545, 1653, 2612, 3221 cm−1; 1H NMR (200 MHz, DMSO-d) δ 1.32 (t, 3H, J=7.0 Hz), 3.44 (m, 4H), 3.74 (m, 4H), 4.58 (t, 2H, J=4.5 Hz), 7.29 (ddd, 1H, 5JH-F=0.6 Hz, J=5.1, 7.7 Hz), 7.82 (m, 6H), 8.47 (s, 1H), 8.52 (s, 1H), 9.16 (te, 1H, J=4.9 Hz), 10.82 (se, 1H).

Workup

  1. customThis compound was prepared
  2. customReaction time at room temperature

Sources & evidence

ORD record
ord-0237f0cfeb1a4d8fba80c2e0e934371f
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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