Acryloyl chloride → HCID 71474497, compound

HRID 1522210Notes

Reaction equation

HRID 1522210 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH:11]1[CH2:19][C:15]2([CH2:18][CH2:17][CH2:16]2)[N:14]([C:20]([O:22]C(C)(C)C)=O)[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[CH2:19][C:15]3([CH2:16][CH2:17][CH2:18]3)[N:14]([C:20](=[O:22])[CH:43]=[CH2:44])[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 162286758-amino-5-Azaspiro[3.5]nonane-5-carboxylic acid 1,1-dimethylethyl esterHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71474497HCID 71474497, compound

Procedure

1-(8-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-5-azaspiro[3.5]nonan-5-yl)prop-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 8-amino-5-azaspiro[3.5]nonane-5-carboxylate, (4-phenoxyphenyl)boronic acid and acryloyl chloride according to general scheme 3 using methods S1, S2, S3, and S4C. HPLC purity: 95%. MS: m/z=456 [M+H]+. 1H NMR (CD3OD) δ 8.28 (s, 1H), 7.15-7.43 (m, 9H), 6.61 (m, 1H), 6.13 (d, 1H), 5.67 (d, 1H), 4.64 (m, 1H), 3.95 (m, 1H), 3.03 (m, 1H), 2.66 (m, 1H), 2.30 (m, 1H), 2.19 (m, 2H), 2.07 (m, 1H), 1.80 (m, 4H), 1.30 (m, 1H).

Sources & evidence

ORD record
ord-a88958c83e324c15ac91241a5e602493
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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