Dichloromethane → HCID 66712594, compound

HRID 1262385Notes

Reaction equation

HRID 1262385 reaction equation
C([O:5][C:6](=[O:27])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:23]2[C:18]([CH:19]=[N:20][C:21]([S:24]([CH3:26])=[O:25])=[N:22]2)=[CH:17][CH:16]=1)(C)(C)C.C(Cl)Cl.FC(F)(F)C(O)=O>>[CH3:26][S:24]([C:21]1[N:20]=[CH:19][C:18]2=[CH:17][CH:16]=[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:7][C:6]([OH:27])=[O:5])[N:23]2[N:22]=1)=[O:25]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66712624HCID 66712624, compound

Product 1

HCID 66712594HCID 66712594, compoundYield 77.3%

Procedure

[2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenoxy]-acetic acid tert-butyl ester (0.298 g, 0.769 mmol), Methylene chloride (11 mL, 170 mmol), and Trifluoroacetic Acid (2.20 mL, 28.5 mmol) were combined and stirred for 18 hours. The product was extracted into dichloromethane and purified by normal phase silica gel chromatography eluting with methanol/dichloromethane to yield a brown solid, [2-(2-Methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenoxy]-acetic acid (197 mg, 77%). LCMS: m/z=332.06 (M+H+); 1H NMR (400 MHz, DMSO-d6) δ 9.30 (s, 1H), 7.86 (d, 1H, J=7.6 Hz), 7.54 (d, 1H, J=4.7 Hz), 7.46 (m, 1H), 7.31 (d, 1H, J=4.7 Hz), 7.14 (m, 2H), 4.77 (s, 2H), 2.92 (s, 3H).

Workup

  1. extractionThe product was extracted into dichloromethane
  2. custompurified by normal phase silica gel chromatography
  3. washeluting with methanol/dichloromethane

Sources & evidence

ORD record
ord-0031fe12ba2b4c4f8857bc18909a2821
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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