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

HRID 2250391Notes

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](O)=[O:31])[CH:3]=1.[NH2:33][C:34]1[C:39]([NH2:40])=[CH:38][C:37]([I:41])=[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:31])[CH2:29][CH2:28][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([NH:8][C:9]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:5]=2)=[CH:38][C:37]([I:41])=[CH:36][N:35]=1

Participants

Conditions

Temperature: 50 °C

Procedure

1.30 g of 3-[4-methyl-6-(trityl-amino)pyridin-2-yl]-propionic acid and 724 mg of 2,3-diamino-5-iodo-pyridine are dissolved in 37 ml of pyridine and sequentially treated with 1.06 g of O-[(ethoxycarbonyl)canomethylene-amino]-N,N,N′,N′-tetramethyl-uronium tetrafluoroborate and 579 μl of diisopropylethyl amine. The reaction mixture is warmed to 50° C. for 24 h. Thereafter the solvents are evaporated in vacuo. The remaining residue is coevaporated twice with toluene yielding 3.55 g of crude product. Purification by chromatography on LiChroprep® NH2 (25-40 μm, Merck, Darmstadt) (75 g, eluent: toluene/ethyl acetate 1:1) affords 1.08 g of the title compound as an amorphous solid. ESI-MS: 640.0 (MH+). TLC: Rf=0.16 (toluene/ethyl acetate 1:1, LiChroprep® NH2 HPTLC).

Workup

customThereafter the solvents are evaporated in vacuo
customPurification by chromatography on LiChroprep® NH2 (25-40 μm, Merck, Darmstadt) (75 g, eluent: toluene/ethyl acetate 1:1)

Sources & evidence

ORD record: ord-263ea1d8e1cc466681738b6da5ab972b
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317021B2

Reaction notes

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