1,4-Dioxa-8-azaspiro(4.5)decane → N-(4-{[2-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)pyrimidin-4-yl]oxy}-1-naphthyl)-3-fluoro-5-morpholin-4-ylbenzamide

HRID 1641179Notes

Reaction equation

HRID 1641179 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[C:42]2([CH2:47][CH2:46][NH:45][CH2:44][CH2:43]2)[O:41][CH2:40][CH2:39]1>>[O:38]1[C:42]2([CH2:47][CH2:46][N:45]([C:21]3[N:20]=[C:19]([O:18][C:11]4[C:12]5[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:8]([NH:7][C:5](=[O:6])[C:4]5[CH:29]=[C:30]([N:32]6[CH2:37][CH2:36][O:35][CH2:34][CH2:33]6)[CH:31]=[C:2]([F:1])[CH:3]=5)=[CH:9][CH:10]=4)[CH:24]=[CH:23][N:22]=3)[CH2:44][CH2:43]2)[O:41][CH2:40][CH2:39]1

Participants

3

Reactant 2

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 595530953-fluoro-N-(4-{[2-(methylsulfonyl)pyrimidin-4-yl]oxy}-1-naphthyl)-5-morpholin-4-ylbenzamide

Product 1

HCID 59553139N-(4-{[2-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)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 1,4-dioxa-8-aza-spiro[4.5]decane according to conditions described in general procedure C. Mp: 115-117° C.; 1H NMR (400 MHz, CDCl3) δ 1.64 (t, J=5.0 Hz, 4 H), 3.26 (t, J=4.3 Hz, 4 H), 3.77 (s, 4 H), 3.88 (t, J=4.7 Hz, 4 H), 3.96 (s, 4 H), 5.98-5.99 (m, 1 H), 6.77 (d, J=11.7 Hz, 1H), 7.07 (d, J=7.8 Hz, 1 H), 7.32-7.34 (m, 2 H), 7.50-7.60 (m, 3 H), 7.90 (d, J=8.2 Hz, 1 H), 8.00 (d, J=8.6 Hz, 1 H), 8.10 (s, 2 H), 8.15-8.17 (m, 1 H).

Sources & evidence

ORD record
ord-cf24b13451634e07921acd1eb9d85d95
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

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