Acrylic Acid → HCID 86721853, compound

HRID 1522279Notes

Reaction equation

HRID 1522279 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=2)[CH:11]=1.[OH:26][CH:27]1[CH2:40][C:29]2([CH2:32][N:31]([C:33]([O:35]C(C)(C)C)=O)[CH2:30]2)[CH2:28]1.[C:41](O)(=O)[CH:42]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:26][CH:27]2[CH2:28][C:29]3([CH2:30][N:31]([C:33](=[O:35])[CH:41]=[CH2:42])[CH2:32]3)[CH2:40]2)[C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([O:16][C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 6581Acrylic AcidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 52987765tert-Butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylateHCID 57655249HCID 57655249, compound

Product 1

HCID 86721853HCID 86721853, compoundYield 21.2%

Procedure

1-(6-((6-amino-5-(4-(pyridin-3-yloxy)phenyl)pyrimidin-4-yl)oxy)-2-azaspiro[3.3]heptan-2-yl)prop-2-en-1-one was prepared 5,6-dichloropyrimidin-4-amine, (4-(pyridin-3-yloxy)phenyl)boronic acid, tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate and acrylic acid with method S1, S2, S3, S4A. Yield 21.2%. 1H NMR (CD3OD) δ 8.31 (m, 2H), 8.13 (s, 1H), 7.52 (m, 1H), 6.97 (m, 1H), 7.41 (d, 2H), 7.19 (m, 2H), 6.25 (m, 2H), 5.75 (m, 1H), 5.24 (m, 1H), 4.21 (d, 2H), 4.03 (d, 2H), 2.72 (m, 2H), 2.25 (m, 2H). HPLC PURITY: 99%, MS: m/z=430[M+H]+

Sources & evidence

ORD record
ord-3ca2f3f47bc241f48f9343cf6c86bc0f
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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