1,3-Dioxolane-2-methanamine, N-methyl- → N-[4-({2-[(1,3-Dioxolan-2-ylmethyl)(methyl)amino]pyrimidin-4-yl}oxy)-1-naphthyl]-3-fluoro-5-morpholin-4-ylbenzamide

HRID 1171275Notes

Reaction equation

HRID 1171275 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]1[CH2:42][CH2:41][O:40][CH:39]1[CH2:43][NH:44][CH3:45]>>[O:38]1[CH2:42][CH2:41][O:40][CH:39]1[CH2:43][N:44]([CH3:45])[C:21]1[N:20]=[C:19]([O:18][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:29]=[C:30]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH:31]=[C:2]([F:1])[CH:3]=3)=[CH:9][CH:10]=2)[CH:24]=[CH:23][N:22]=1

Participants

3

Reactant 2

HCID 5417541,3-Dioxolane-2-methanamine, N-methyl-HCID 595530953-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide

Product 1

HCID 59553263N-[4-({2-[(1,3-Dioxolan-2-ylmethyl)(methyl)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 [1,3]dioxolan-2-ylmethyl-methylamine according to conditions described in general procedure C. Mp: 111-112° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.75-3.96 (m, 8 H), 3.27 (m, 4 H), 3.80 (m, 4H), 4.75-5.0 (m, 2 H), 6.27 (d, J=5.1Hz, 1 H), 7.05 (d, J=12.5 Hz, 1 H), 7.28 (d, J=8.8 Hz, 1 H), 7.42-7.62 (m, 5 H), 7.84 (d, J=7.7 Hz, 1 H), 7.99-8.01 (m, 1 H), 8.28 (d, J=5.5 Hz, 1 H), 10.47 (s, 1 H).

Sources & evidence

ORD record
ord-eb83a8f745f54d0488b68aa1ba8c1fb2
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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