Propiolic Acid → HCID 86721796, compound

HRID 1522198Notes

Reaction equation

HRID 1522198 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[CH2:10]([N:17]1[CH:21]=[C:20](B(O)O)[CH:19]=[N:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:25][CH2:26][C@@H:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35]C(C)(C)C)=O)[CH2:29][C@H:28]1[OH:40].[C:41](O)(=O)[C:42]#C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:25][CH2:26][C@@H:27]2[CH2:32][CH2:31][N:30]([C:33](=[O:35])[C:41]#[CH:42])[CH2:29][C@H:28]2[OH:40])[C:2]=1[C:20]1[CH:19]=[N:18][N:17]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:21]=1

Participants

5

Reactant 4

HCID 10110Propiolic AcidHCID 33528811-Benzyl-1H-pyrazole-4-boronic acidHCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721796HCID 86721796, compound

Procedure

1-((3S,4S)-4-(((6-amino-5-(1-benzyl-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)prop-2-yn-1-one was prepared from 5,6-dichloropyrimidin-4-amine, (1-benzyl-1H-pyrazol-4-yl)boronic acid, (3S,4S)-tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate and propiolic acid according to general scheme 3 using methods S1, S2, S3, and S4A. HPLC purity: 99%. MS: m/z=432 [M+H]+. 1H NMR (CD3OD) δ 8.22 (s, 1H), 7.84 (s, 1H), 7.69 (s, 1H), 7.40 (m, 5H), 4.43 (m, 2H), 4.01 (d, 1H), 3.62 (m, 1H), 3.61 (m, 1H), 3.29 (m, 1H), 3.03 (m, 1H), 2.60 (m, 1H), 1.76 (m, 3H), 1.24 (m, 1H), 1.21 (m, 1H).

Sources & evidence

ORD record
ord-9a97da88c386474eb409a62cae649ca8
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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