Acryloyl chloride → HCID 86721806, compound

HRID 1522208Notes

Reaction equation

HRID 1522208 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH:11]1[C:14]2([CH2:19][CH2:18][N:17]([C:20]([O:22]C(C)(C)C)=O)[CH2:16][CH2:15]2)[CH2:13][CH2:12]1.[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]([NH:10][CH:11]2[C:14]3([CH2:15][CH2:16][N:17]([C:20](=[O:22])[CH:43]=[CH2:44])[CH2:18][CH2:19]3)[CH2:13][CH2:12]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 25212937tert-Butyl 1-amino-7-azaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 86721806HCID 86721806, compound

Procedure

1-(1-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-7-azaspiro[3.5]nonan-7-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 1-amino-7-azaspiro[3.5]nonane-7-carboxylate, (4-phenoxyphenyl)boronic acid and acryloyl chloride according to general scheme 3 using methods S1, S2, S3, and S4C. HPLC purity: 99%. MS: m/z=456 [M+H]+. 1H NMR (CD3OD) δ 8.24 (s, 1H), 7.11-7.50 (m, 9H), 6.73 (m, 1H), 6.18 (d, 1H), 5.71 (d, 1H), 4.53 (m, 1H), 4.21 (m, 1H), 3.83 (m, 1H), 3.18 (m, 1H), 2.95 (m, 1H), 2.27 (m, 2H), 2.06 (m, 1H), 1.86 (m, 2H), 1.68 (m, 3H), 1.37 (m, 1H).

Sources & evidence

ORD record
ord-714386828468457bbf31c20e1526c407
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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