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

HRID 505425노트

반응식

HRID 505425 반응식
[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

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 218827665-Iodopyridine-2,3-diamineHCID 684615903-[4-Methyl-6-(trityl-amino)-pyridin-2-yl]propionic acid

생성물 1

HCID 68461097N-(2-Amino-5-iodo-pyridin-3-yl)-3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propionamide수율 54.9%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
50 °C

실험 절차

1.30 g of 3-[4-methyl-6-(trityl-amino)-pyridin-2-yl]-propionic acid 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 tetrafluoro-borate 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).

후처리

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

출처 및 근거

ORD 기록
ord-3a7d2db97ccf4dcea8e6c9280c3f517c
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781453B2

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