(4-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-acetic acid tert-butyl ester → (4-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-acetic acid

HRID 1262349Notes

Reaction equation

HRID 1262349 reaction equation
C([O:5][C:6](=[O:40])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[CH:25][C:24]4=[CH:27][CH:28]=[C:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[O:36][CH3:37])[N:23]4[N:22]=3)=[C:16]([O:38][CH3:39])[CH:15]=2)[CH2:10][CH2:9]1)(C)(C)C>Cl.O1CCOCC1>[CH3:39][O:38][C:16]1[CH:15]=[C:14]([CH:11]2[CH2:12][CH2:13][N:8]([CH2:7][C:6]([OH:40])=[O:5])[CH2:9][CH2:10]2)[CH:19]=[CH:18][C:17]=1[NH:20][C:21]1[N:26]=[CH:25][C:24]2=[CH:27][CH:28]=[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])[N:23]2[N:22]=1

Participants

4

Reactant 1

HCID 66712696(4-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 66711967(4-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-acetic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of] (4-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-acetic acid tert-butyl ester (73 mg, 0.13 mmol) in 2 mL of 4N HCl in dioxane was stirred at RT. After 18 h, solvent was evaporated and the mixture was triturated with ether. A solid was obtained which was filtered, washed with ether (twice) and dried. The product, (4-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-acetic acid was isolated as a pale yellow hygroscopic solid (54 mg, 82%). LCMS (E/I+) 488 (M+H). NMR 1H (DMSO-d6)-10.1 (br s, 1H), 8.96 (s, 1H0, 8.05 (d, 1H, J=8.24 Hz), 7.81 (d, 1H, J=7.49 Hz), 7.68 (s, 1H), 7.46 (m, 1H), 7.41 (d, 1H, J=7.96 Hz), 7.21 (d, 1H, J=8.34 Hz), 7.11 (d, 1H, J=7.45 Hz), 7.08 (m, 1H), 6.98 (m, 2H), 6.70 (d, 1H, J=7.32 Hz), 4.16 (br s, 2H), 4.05-3.1 (series of m and s along with the water peak, 10H), 2.8 (m, 1H), 2.03 (m, 4H).

Workup

  1. customsolvent was evaporated
  2. customthe mixture was triturated with ether
  3. customA solid was obtained which
  4. filtrationwas filtered
  5. washwashed with ether (twice) and
  6. customdried

Sources & evidence

ORD record
ord-e576b76012374dc79d4a16b966fbcd96
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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