Tyramine → 4-[2-(4-{3-[(3(S)-Methyl-piperidin-4(R)-ylamino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

HRID 2386540Notes

Reaction equation

C(OC([N:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[CH:29][N:28]=[C:27](Cl)[N:26]=3)[CH:20]=2)[C@@H:13]([CH3:32])[CH2:12]1)=O)C1C=CC=CC=1.[NH2:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1>>[CH3:32][C@@H:13]1[C@H:14]([NH:17][CH2:18][C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:33][CH2:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=4)[N:26]=3)[CH:22]=[CH:23][CH:24]=2)[CH2:15][CH2:16][NH:11][CH2:12]1

Participants

Reactant 2

HCID 5610Tyramine

HCID 866033194(R)-[3-(2-Chloro-pyrimidin-4-yl)-benzylamino]-3(S)-methyl-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 586036574-[2-(4-{3-[(3(S)-Methyl-piperidin-4(R)-ylamino)-methyl]-phenyl}-pyrimidin-2-ylamino)-ethyl]-phenol

Procedure

Intermediate 136 was coupled with tyramine following procedure F. The resulting product was deprotected following procedure G3. LC-MS showed the product had the expected M+H+ of 418. 1H NMR (Varian 300 MHz, CD3OD, shifts relative to the solvent peak at 3.3 ppm) δ 8.63 (s, 1H) 8.36 (d, 2H) 7.95 (d, 1H) 7.75 (t, 1H) 7.67 (d, 1H) 7.15 (d, 2H) 6.71 (d, 2H) 4.50 (s, 2H) 3.96 (m, 1H) 3.80 (m, 1H) 3.72 (m, 1H) 3.56 (d, 1H) 3.34 (d, 1H) 3.20 (t, 2H) 2.96 (t, 2H) 2.80 (m, 1H) 2.38 (dd, 2H) 1.36 (d, 3H).

Sources & evidence

ORD record: ord-f2c0714652fc4caca09ff478df0481a7
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268822B2

Reaction notes

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