Acrylic Acid → HCID 86721795, compound

HRID 1522197Notes

Reaction equation

HRID 1522197 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=O)[CH2:14][C@H:13]1[OH:25].[CH2:26]([N:33]1[CH:37]=[C:36](B(O)O)[CH:35]=[N:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:41](O)(=O)[CH:42]=C>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][C@@H:12]2[CH2:17][CH2:16][N:15]([C:18](=[O:20])[CH:41]=[CH2:42])[CH2:14][C@H:13]2[OH:25])[C:2]=1[C:36]1[CH:35]=[N:34][N:33]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:37]=1

Participants

5

Reactant 4

HCID 6581Acrylic AcidHCID 33528811-Benzyl-1H-pyrazole-4-boronic acidHCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 86721795HCID 86721795, 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-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, (3S,4S)-tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate, (1-benzyl-1H-pyrazol-4-yl)boronic acid and acrylic acid according to general scheme 3 using methods S1, S2, S3, and S4A. HPLC purity: 99%. MS: m/z=434 [M+H]+. 1H NMR (CD3OD) δ 8.22 (s, 1H), 7.84 (s, 1H), 7.60 (s, 1H), 7.40 (m, 5H), 6.76 (m, 1H), 6.21 (d, 1H), 5.74 (d, 1H), 5.43 (s, 2H), 4.53 (m, 1H), 4.08 (m, 1H), 3.61 (m, 2H), 3.03 (m, 1H), 2.72 (m, 1H), 1.89 (m, 1H), 1.72 (m, 2H), 1.21 (m, 1H), 1.01 (m, 1H).

Sources & evidence

ORD record
ord-3cea0d349e3b4f2cbaa6865c677eb1be
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

Loading…