(S)-1-Boc-3-methylpiperazine → 4-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3-(S)-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2386443Notes

Reaction equation

HRID 2386443 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)[CH:5]=[CH:4][N:3]=1.[C:16]([N:23]1[CH2:28][CH2:27][NH:26][C@@H:25]([CH3:29])[CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][N:26]([CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH:9]=2)[C@@H:25]([CH3:29])[CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

3

Reactant 2

HCID 7023035(S)-1-Boc-3-methylpiperazineHCID 249019653-(2-Chloro-pyrimidin-4-yl)-benzaldehyde

Product 1

HCID 866032844-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-3-(S)-methyl-piperazine-1-carboxylic acid tert-butyl ester

Procedure

Intermediate 1 was coupled with 4-boc-2-(S)-methyl-piperazine following procedure B. LC-MS showed the product had the expected M+H+ of 403. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.6 (d, 1H) 8.0 (m, 2H) 7.6 (d, 1H) 7.5 (m, 2H) 4.8 (d, 1H) 4.1 (m, 1H) 3.6 (m, 2H) 3.3 (m, 1H) 3.0 (m, 2H) 2.5 (m, 2H) 1.4 (s, 9H) 1.1 (m, 3H).

Sources & evidence

ORD record
ord-a4ec1d5b6ace4fd1ab07ef089af85547
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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