2-Fluoronicotinic acid → HCID 71092874, compound

HRID 1522116Notes

Reaction equation

HRID 1522116 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=O)[CH2:14][CH2:13]1.[O:25]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[F:41][C:42]1[N:50]=[CH:49][CH:48]=[CH:47][C:43]=1C(O)=O>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([C:18]([C:43]3[C:42]([F:41])=[N:50][CH:49]=[CH:48][CH:47]=3)=[O:20])[CH2:16][CH2:17]2)[C:2]=1[C:29]1[CH:30]=[CH:31][C:26]([O:25][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 4

HCID 960892-Fluoronicotinic acidHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27343774-Phenoxyphenylboronic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71092874HCID 71092874, compound

Procedure

(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)methyl)piperidin-1-yl)(2-fluoropyridin-3-yl)methanone was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(aminomethyl)piperidine-1-carboxylate, (4-phenoxyphenyl)boronic acid, and 2-fluoronicotinic acid using methods B, C, D, and E. HPLC purity: 100%. MS: m/z=499 [M+H]+. 1H-NMR (DMSO-d6) □δ 8.28 (s, 1H), 8.25 (d, 1H), 7.92 (t, 1H), 7.39-7.36 (m, 3H), 7.20-6.90 (m, 10H), 4.39 (d, 1H), 3.28 (d, 1H), 3.19 (m, 2H), 2.94 (t, 1H), 2.70 (t, 1H), 1.78 (s, 1H), 1.63 (d, 1H), 1.49 (d, 1H), 1.05-0.92 (m, 2H).

Sources & evidence

ORD record
ord-49b4ce29f2724263a1a9601956134b11
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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