3-Thiophenamine, tetrahydro-, 1,1-dioxide → N-[4-({2-[(1,1-Dioxidotetrahydro-3-thienyl)amino]pyrimidin-4-yl}oxy)-1-naphthyl]-3-fluoro-5-morpholin-4-ylbenzamide

HRID 1641173Notes

Reaction equation

HRID 1641173 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[C:30]([N:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:31]=1)[C:5]([NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](S(C)(=O)=O)[N:20]=2)=[CH:10][CH:9]=1)=[O:6].[O:38]=[S:39]1(=[O:45])[CH2:43][CH2:42][CH:41]([NH2:44])[CH2:40]1>>[O:38]=[S:39]1(=[O:45])[CH2:43][CH2:42][CH:41]([NH:44][C:21]2[N:20]=[C:19]([O:18][C:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([NH:7][C:5](=[O:6])[C:4]4[CH:29]=[C:30]([N:32]5[CH2:33][CH2:34][O:35][CH2:36][CH2:37]5)[CH:31]=[C:2]([F:1])[CH:3]=4)=[CH:9][CH:10]=3)[CH:24]=[CH:23][N:22]=2)[CH2:40]1

Participants

3

Reactant 2

HCID 228073-Thiophenamine, tetrahydro-, 1,1-dioxideHCID 595530953-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide

Product 1

HCID 59553196N-[4-({2-[(1,1-Dioxidotetrahydro-3-thienyl)amino]pyrimidin-4-yl}oxy)-1-naphthyl]-3-fluoro-5-morpholin-4-ylbenzamide

Procedure

Compound is prepared from 3-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide and 1,1-Dioxo-tetrahydro-1λ6-thiophen-3-ylamine according to conditions described in general procedure C. Mp: 150-151° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.04 (s, 2 H), 2.30 (s, 1 H), 2.88 (s, 2 H), 3.07 (s, 2 H), 3.26 (t, J=4.4 Hz, 4 H), 3.77 (t, J=4.8 Hz, 4 H), 4.56 (s, 1 H), 6.49 (s, 1 H), 7.04 (d, J=12.4 Hz, 1 H), 7.26 (d, J=8.8 Hz, 1 H), 7.43 (d, J=8.0 Hz, 1 H), 7.47 (s, 1 H), 7.56-7.61 (m, 3 H), 7.81-7.84 (m, 1 H), 7.99 (d, J=7.6 Hz, H), 8.30 (d, J=4.0 Hz, 1H), 10.46 (s, 1 H).

Sources & evidence

ORD record
ord-2b3afd158e5b4147b87ff606ca9f64c1
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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