Acryloyl chloride → HCID 86721783, compound

HRID 1522182Notes

Reaction equation

HRID 1522182 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[CH2:10]1[C:14]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH2:13][CH2:12][N:11]1[C:20]([O:22]C(C)(C)C)=O.[O:27]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[C:43](Cl)(=O)[CH:44]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([N:17]2[CH2:16][CH2:15][C:14]3([CH2:10][N:11]([C:20](=[O:22])[CH:43]=[CH2:44])[CH2:12][CH2:13]3)[CH2:19][CH2:18]2)[C:2]=1[C:31]1[CH:32]=[CH:33][C:28]([O:27][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 34178604tert-Butyl 2,8-diazaspiro[4.5]decane-2-carboxylate

Product 1

HCID 86721783HCID 86721783, compound

Procedure

1-(8-(6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decan-2-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 2,8-diazaspiro[4.5]decane-2-carboxylate, (4-phenoxyphenyl)boronic acid, and acryloyl chloride in four steps according to general scheme 2, using methods I, C, D and G. MS: m/z=456 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 8.33 (s, 1H), 7.44 (t, 2H), 7.35 (t, 2H), 7.19 (t, 1H), 7.10 (d, 3H), 6.91 (bs, 2H), 6.53 (m, 1H), 6.13 (d, 1H), 5.72-5.60 (m, 1H), 3.70-3.10 (m, 11H), 1.85 (t, 1H), 1.76 (m, 2H).

Sources & evidence

ORD record
ord-25eebb796ce340ee9054697001cce3fd
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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