Propiolic Acid → HCID 86721792, compound

HRID 1522192Notes

Reaction equation

HRID 1522192 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][CH2:12][CH:13]1[CH2:16][N:15]([C:17]([O:19]C(C)(C)C)=O)[CH2:14]1.[O:24]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:40](O)(=O)[C:41]#C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][CH2:12][CH:13]2[CH2:14][N:15]([C:17](=[O:19])[C:40]#[CH:41])[CH2:16]2)[C:2]=1[C:28]1[CH:29]=[CH:30][C:25]([O:24][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 10110Propiolic AcidHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 44630603tert-Butyl 3-(2-aminoethyl)azetidine-1-carboxylate

Product 1

HCID 86721792HCID 86721792, compound

Procedure

1-(3-(2-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)ethyl)azetidin-1-yl)prop-2-yn-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 3-(2-aminoethyl)azetidine-1-carboxylate, (4-phenoxyphenyl)boronic acid and propiolic acid according to general scheme 3 using methods S1, S2, S3 and S4A. HPLC purity: 99%. MS: m/z=414[M+H]+. 1H NMR (CD3OD) δ 8.27 (s, 1H), 7.14-7.45 (m, 9H), 4.33 (t, 1H), 4.09 (dd, 1H), 3.91 (m, 2H), 3.68 (dd, 1H), 3.49 (t, 2H), 2.69 (m, 1H), 1.87 (m, 2H).

Sources & evidence

ORD record
ord-82ed5d35dad542369a250c0663637cb3
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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