2-(3,5-Difluorophenyl)ethan-1-amine → HCID 58603417, compound

HRID 14960Notes

Reaction equation

HRID 14960 reaction equation
C(OC([N:8]1[CH:13]([CH3:14])[CH2:12][N:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[N:23]=3)[CH:17]=2)[CH2:10][CH:9]1C)=O)(C)(C)C.[F:30][C:31]1[CH:32]=[C:33]([CH2:38][CH2:39][NH2:40])[CH:34]=[C:35]([F:37])[CH:36]=1>>[CH:10]12[CH2:14][CH:13]([NH:8][CH2:9]1)[CH2:12][N:11]2[CH2:15][C:16]1[CH:17]=[C:18]([C:22]2[CH:27]=[CH:26][N:25]=[C:24]([NH:40][CH2:39][CH2:38][C:33]3[CH:34]=[C:35]([F:37])[CH:36]=[C:31]([F:30])[CH:32]=3)[N:23]=2)[CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 36736652-(3,5-Difluorophenyl)ethan-1-amineHCID 866033254-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2,6-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603417HCID 58603417, compound

Procedure

Intermediate 142 was coupled with 2-(3,5-difluoro-phenyl)-ethylamine following procedure F. The resulting product was deprotected following procedure G2. LC-MS showed the product had the expected M+H+ of 422. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.78 (s, 1H) 8.38 (d, 2H) 8.00 (d, 1H) 7.77 (t, 1H) 7.68 (d, 1H) 7.00 (d, 2H) 6.75 (t, 1H) 4.84 (d, 1H) 4.65 (s, 2H) 4.60 (d, 1H) 4.24 (d, 1H) 4.10 (d, 1H) 3.89 (d, 1H) 3.68 (d, 1H) 3.63 (t, 2H) 3.07 (t, 2H) 2.86 (d, 1H) 2.37 (d, 1H).

Sources & evidence

ORD record
ord-dff5ac739c554992b1aa4893d497ecca
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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