1-Boc-4-(aminomethyl)piperidine → HCID 71093008, compound

HRID 1522278Notes

Reaction equation

HRID 1522278 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][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36]C(C)(C)C)=O)[CH2:30][CH2:29]1.[N:41]1([CH2:46]/[CH:47]=[CH:48]/C(O)=O)[CH2:45][CH2:44][CH2:43][CH2:42]1>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:26][CH2:27][CH:28]2[CH2:29][CH2:30][N:31]([C:34](=[O:36])/[CH:48]=[CH:47]/[CH2:46][N:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)[CH2:32][CH2:33]2)[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 7368171-Boc-4-(aminomethyl)piperidineHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamineHCID 58075148HCID 58075148, compound

Product 1

HCID 71093008HCID 71093008, compoundYield 9.1%

Procedure

(E)-1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)-4-(pyrrolidin-1-yl)but-2-en-1-one was prepared 5,6-dichloropyrimidin-4-amine, 4-phenoxyphenylboronic acid, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate and (E)-4-(pyrrolidin-1-yl)but-2-enoic acid with method S1, S2, S3, S4A. Yield 9.1%. 1H NMR (CD3OD) δ 8.31 (m, 2H), 7.19-7.47 (m, 9H), 6.92 (d, 1H), 6.63 (m, 1H), 4.54 (d, 1H), 4.07 (d, 1H), 4.01 (d, 2H), 3.64 (s, 1H), 3.12 (t, 2H), 2.75 (t, 1H), 2.20 (s, 1H), 2.03 (s, 1H), 1.75 (t, 2H), 1.11 (t, 2H). HPLC PURITY: 91%, MS: m/z=513[M+H]+

Sources & evidence

ORD record
ord-c38c59bb30b34521aed1161a23d6d0bd
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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