2-(3,5-Difluorophenyl)ethan-1-amine → [2-(3,5-Difluoro-phenyl)-ethyl]-(4-{3-[3(S)-(1H-indol-3-ylmethyl)-piperazin-1-ylmethyl]-phenyl}-pyrimidin-2-yl)-amine

HRID 14903Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[N:22]=3)[CH:16]=2)[CH2:10][CH:9]1[CH2:28][C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31][CH:30]=1)=O)(C)(C)C.[F:38][C:39]1[CH:40]=[C:41]([CH2:46][CH2:47][NH2:48])[CH:42]=[C:43]([F:45])[CH:44]=1>>[F:38][C:39]1[CH:40]=[C:41]([CH2:46][CH2:47][NH:48][C:23]2[N:22]=[C:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][N:11]4[CH2:12][CH2:13][NH:8][C@@H:9]([CH2:28][C:29]5[C:37]6[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=6)[NH:31][CH:30]=5)[CH2:10]4)[CH:16]=3)[CH:26]=[CH:25][N:24]=2)[CH:42]=[C:43]([F:45])[CH:44]=1

Participants

Reactant 2

HCID 36736652-(3,5-Difluorophenyl)ethan-1-amine

HCID 866033034-[3-(2-Chloro-pyrimidin-4-yl)-benzyl]-2-(1H-indol-3-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58603671[2-(3,5-Difluoro-phenyl)-ethyl]-(4-{3-[3(S)-(1H-indol-3-ylmethyl)-piperazin-1-ylmethyl]-phenyl}-pyrimidin-2-yl)-amine

Procedure

Intermediate 109 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 540. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.59 (s, 1H), 8.34 (d, 1H), 8.29 (d, 1H), 7.84 (d, 1H), 7.60 (m, 3H), 7.33 (d, 1H), 7.26 (s, 1H), 6.98 (m, 4H), 6.72 (s, 1H), 4.63 (s, 2H), 4.16 (m, 1H), 4.04 (s, 2H), 3.49 (m, 4H), 3.26 (m, 4H), 3.05 (t, 2H).

Sources & evidence

ORD record: ord-6c163847b9144d87b3e1406f9a64e3b8
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732444B2

Reaction notes

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