Acryloyl chloride → 1-(2-(6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)-2,7-diazaspiro[3.5]nonan-7-yl)prop-2-en-1-one

HRID 1522181Notes

Reaction equation

HRID 1522181 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[CH2:10]1[C:13]2([CH2:18][CH2:17][N:16]([C:19]([O:21]C(C)(C)C)=O)[CH2:15][CH2:14]2)[CH2:12][NH:11]1.[O:26]([C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:42](Cl)(=O)[CH:43]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([N:11]2[CH2:10][C:13]3([CH2:14][CH2:15][N:16]([C:19](=[O:21])[CH:42]=[CH2:43])[CH2:17][CH2:18]3)[CH2:12]2)[C:2]=1[C:30]1[CH:31]=[CH:32][C:27]([O:26][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 13140Acryloyl chlorideHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 24820512tert-Butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 714744451-(2-(6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)-2,7-diazaspiro[3.5]nonan-7-yl)prop-2-en-1-one

Procedure

1-(2-(6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)-2,7-diazaspiro[3.5]nonan-7-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 2,7-diazaspiro[3.5]nonane-7-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=442 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 8.31 (s, 1H), 7.43 (t, 2H), 7.34 (d, 2H), 7.18 (t, 1H), 7.11 (d, 4H), 7.04 (bs, 1H), 6.77 (dd, 1H), 6.06 (dd, 1H), 5.65 (dd, 1H), 3.10-3.90 (m, 8H), 1.59 (s, 4H).

Sources & evidence

ORD record
ord-6ffc42f4a730459a8f05acdd5a4f891f
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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