Acryloyl chloride → 1-(7-(6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2-yl)prop-2-en-1-one

HRID 1522183Notes

Reaction equation

HRID 1522183 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([CH2:18][CH2:17][NH:16][CH2:15]2)[CH2:13][CH2:12][N:11]1[C:19]([O:21]C(C)(C)C)=O.[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:16]2[CH2:17][CH2:18][C:14]3([CH2:10][N:11]([C:19](=[O:21])[CH:42]=[CH2:43])[CH2:12][CH2:13]3)[CH2:15]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 23282813tert-Butyl 2,7-diazaspiro[4.4]nonane-2-carboxylateHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 867217841-(7-(6-Amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2-yl)prop-2-en-1-one

Procedure

1-(7-(6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)-2,7-diazaspiro[4.4]nonan-2-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 2,7-diazaspiro[4.4]nonane-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=442 [M+H]+. 1H-NMR (400 MHz, DMSO-d6) δ 8.33 (s, 1H), 7.43 (t, 2H), 7.35 (d, 2H), 7.18 (m, 3H), 7.10 (d, 2H), 6.97 (bs, 2H), 6.54 (ddd, 1H), 6.11 (d, 1H), 5.71-5.60 (m, 1H), 3.70-3.10 (m, 6H), 1.77 (t, 1H), 1.68 (t, 1H), 1.39 (bs, 4H).

Sources & evidence

ORD record
ord-0e36f39148734ca6998121033fc0cdac
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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