4-Hydroxymethylpyridine → (1-{4-[3-Chloro-4-(pyridin-4-ylmethoxy)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-piperidin-4-yl)-carbamic acid, tert-butyl ester

HRID 1829936노트

반응식

HRID 1829936 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3=[C:16]([CH2:19][N:20]4[CH2:25][CH2:24][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:22][CH2:21]4)[CH:17]=[CH:18][N:14]3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:54][C:55]1[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:15]3=[C:16]([CH2:19][N:20]4[CH2:21][CH2:22][CH:23]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH2:24][CH2:25]4)[CH:17]=[CH:18][N:14]3[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:54][C:55]1[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=1

참가 물질

6

반응물 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21031521{1-[4-(3-Chloro-4-hydroxy-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl]-piperidin-4-yl}-carbamic acid, tert-butyl ester

생성물 1

HCID 21031526(1-{4-[3-Chloro-4-(pyridin-4-ylmethoxy)-phenylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-piperidin-4-yl)-carbamic acid, tert-butyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 21A (0.047 g, 0.1 mmol), triphenylphosphine (79 mg, 0.3 mmol), and 4-hydroxymethylpyridine (22 mg, 0.2 mmol) in dry THF was added diethyl azodicarboxylate (0.047 ml, 0.3 mmol). The mixture was stirred at room temperature overnight and purified by preparative HPLC to give Compound 21B as a colorless semi-solid (TFA salt). Analytical HPLC retention time=2.303 min. (Chromolith Speed ROD column 4.6×50 mm, 10–90% aqueous methanol over 4 minutes containing 0.2% trifluoroacetic acid, 4 mL/min, monitoring at 254 nm) and a LC/MS M++1=564+.

후처리

  1. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-ae2ab1793b4945ae928e5cc8d4c1948c
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07064203B2

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