4-Nitrophenethylamine → HCID 69524607, compound

HRID 216162Notes

Reaction equation

[N+]([C:4]1C=CC(CCN)=CC=1)([O-])=O.[CH3:13][O:14][C:15]1N=[C:19]([NH:21][C@@H:22]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:23]([OH:25])=[O:24])[CH:18]=[C:17]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[CH:36]=2)[N:16]=1>>[CH3:13][O:14][C:15]1[CH:4]=[C:19]([NH:21][C@@H:22]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=2)[C:23]([OH:25])=[O:24])[CH:18]=[C:17]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[CH:36]=2)[N:16]=1

Participants

Reactant 2

HCID 951534-Nitrophenethylamine

HCID 53319215HCID 53319215, compound

Product 1

HCID 69524607HCID 69524607, compound

Procedure

By proceeding in a similar manner to Example 43(b) but substituting L-O-methyl tyrosine for 2-(4-nitro-phenyl)-ethylamine in Step 3 there is prepared (2S)-2-[2-Methoxy-6-(3-methoxy-phenyl)-pyrimidin-4-ylamino]-3-(4-methoxy-phenyl)-propionic acid [40.2 mg, 45%, Example 43(n)] as a solid. LC/MS: RT=2.38 minutes, MS: 410 (M+H). 1H NMR [300 MHz, (CD3)2SO]: □12 (1H, br s), 7.62 (1H, m), 7.49 (1H, m), 7.38 (1H, m), 7.18 (2H, m), 7 (1H, m), 6.8 (2H, m), 6.73 (1H, s), 4.59 (1H, m), 3.8 (3H, s), 3.78 (3H, s), 3.68 (3H, s), 3.1 (1H, m), 2.94 (1H, m). IC50=548 nM

Sources & evidence

ORD record: ord-88707b61edf6455fbb1829ce899f853b
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193183B2

Reaction notes

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