3-(Morpholin-4-yl)propanoic acid → 1-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-3-morpholinopropan-1-one

HRID 1522288Notes

Reaction equation

HRID 1522288 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[O:10]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH2:26][CH2:27][C@@H:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36]C(C)(C)C)=O)[CH2:30][C@H:29]1[OH:41].[O:42]1[CH2:47][CH2:46][N:45]([CH2:48][CH2:49]C(O)=O)[CH2:44][CH2:43]1>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:26][CH2:27][C@@H:28]2[CH2:33][CH2:32][N:31]([C:34](=[O:36])[CH2:49][CH2:48][N:45]3[CH2:46][CH2:47][O:42][CH2:43][CH2:44]3)[CH2:30][C@H:29]2[OH:41])[C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 4

HCID 4108133-(Morpholin-4-yl)propanoic acidHCID 27343774-Phenoxyphenylboronic acidHCID 11075229trans-1-Boc-4-aminomethyl-3-hydroxypiperidineHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 710929031-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-3-morpholinopropan-1-oneYield 30.5%

Procedure

1-((3S,4S)-4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)-3-hydroxypiperidin-1-yl)-3-morpholinopropan-1-one was prepared 5,6-dichloropyrimidin-4-amine, 4-phenoxyphenylboronic acid, (3S,4S)-tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate and 3-morpholinopropanoic acid with method S1, S2, S3, S4A. Yield 30.5%. 1H NMR (CD3OD) δ 8.26 (s, 1H), 7.14-7.40 (m, 9H), 4.48 (dd, 1H), 3.88 (t, 1H), 3.66 (m, 5H), 3.28 (m, 1H), 3.00 (m, 1H), 2.33-2.61 (m, 9H), 1.49 (s, 2H), 1.20 (m, 1H). HPLC PURITY: 99%, MS: m/z=533[M+H]+

Sources & evidence

ORD record
ord-b9146df8a8764c37841e3c4282dd773c
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

Loading…