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 1829936Notes

Reaction equation

HRID 1829936 reaction equation
[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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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+.

Workup

  1. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-ae2ab1793b4945ae928e5cc8d4c1948c
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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