Diisopropylethylamine → N-[2-Amino-5-(4-chloro-phenyl)-pyridin-3-yl]3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propionamide

HRID 505424Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=[C:4]([CH2:28][CH2:29][C:30]([OH:32])=O)[CH:3]=1.[NH2:33][C:34]1[C:39]([NH2:40])=[CH:38][C:37]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)=[CH:36][N:35]=1.C(N(C(C)C)CC)(C)C>N1C=CC=CC=1>[NH2:33][C:34]1[C:39]([NH:40][C:30](=[O:32])[CH2:29][CH2:28][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([NH:8][C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:5]=2)=[CH:38][C:37]([C:41]2[CH:42]=[CH:43][C:44]([Cl:47])=[CH:45][CH:46]=2)=[CH:36][N:35]=1

Participants

Conditions

Temperature: 40 °C

Procedure

300 mg of 3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propionic acid (compound C4) and 156 mg of 2,3-diamino-5-(4-chloro-phenyl)-pyridine (compound F4) are dissolved in 13 ml of pyridine and sequentially treated with 280 mg of O-[(ethoxycarbonyl)canomethylene-amino]—N,N,N′,N′-tetramethyl-uronium tetrafluoroborate and 153 μl of diisopropylethyl amine. The reaction mixture is warmed to 40° C. for 120 h. Purification of the crude product by chromatography on silica gel (eluent: dichloromethane/methanol 8:1) afforded 405 mg of the title compound as an oil. ESI-MS: 624.1/626.1 (MH+, 100%/38%). TLC: Rf=0.32 (dichloromethane/methanol 8:1).

Workup

customPurification of the crude product by chromatography on silica gel (eluent: dichloromethane/methanol 8:1)

Sources & evidence

ORD record: ord-ff175323f16d41c3a7aebad482edc819
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781453B2

Reaction notes

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