Trifluoroacetic acid → HCID 9936698, compound

HRID 857923Notes

Reaction equation

HRID 857923 reaction equation
[CH2:1]([C:3]1[C:4]([NH:29][C:30]([O:32][CH2:33][C@@H:34]2[CH2:39][O:38][CH2:37][CH2:36][N:35]2C(OC(C)(C)C)=O)=[O:31])=[CH:5][N:6]2[C:11]=1[C:10]([NH:12][C:13]1[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[N:17]=[CH:16]3)=[N:9][CH:8]=[N:7]2)[CH3:2].FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH2:1]([C:3]1[C:4]([NH:29][C:30](=[O:31])[O:32][CH2:33][C@@H:34]2[CH2:39][O:38][CH2:37][CH2:36][NH:35]2)=[CH:5][N:6]2[C:11]=1[C:10]([NH:12][C:13]1[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[N:17]=[CH:16]3)=[N:9][CH:8]=[N:7]2)[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 60017378HCID 60017378, compound

Product 1

HCID 9936698HCID 9936698, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[[[[[5-ethyl-4-[[1-(phenylmethyl)-1H-indazol-5-yl]amino]pyrrolo[2,1-f][1,2,4]triazin-6-yl]amino]carbonyl]oxy]methyl]-4-morpholinecarboxylic acid, (3S)-1,1-dimethylethyl ester (14.0 g, 22.3 mmol) was dissolved in methylene chloride (250 mL) and treated with trifluoroacetic acid (40 mL). The resulting solution was stirred for 18 h, then neutralized by the addition of saturated aqueous sodium carbonate. The organic phase was separated and dried over magnesium sulfate. Filtration and concentration of the filtrate gave 11.4 g of [5-ethyl-4-[[(1-phenylmethyl)-1H-indazol-5-yl]amino]pyrrolo[2,1-f][1,2,4]triazin-6-yl]-carbamic acid, (3S)-3-morpholinylmethyl ester as a yellow oil. This material was re-dissolved in methylene chloride (100 mL) and treated with 1M hydrochloric acid in ether (21.7 mL, 21.7 mmol). The solution was stirred for 30 min then concentrated under reduced pressure. Drying of the residue under high vacuum (0.5 mmHg) overnight afforded 11.6 g (92%) of [5-ethyl-4-[[(1-phenylmethyl)-1H-indazol-5-yl]amino]pyrrolo[2,1-f][1,2,4]triazin-6-yl]-carbamic acid, (3S)-3-morpholinylmethyl ester hydrochloride as an off-white solid.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationFiltration and concentration of the filtrate

Sources & evidence

ORD record
ord-e4b90a2f4f674112a132f8eac85fb859
Source dataset
uspto-grants-2006_12
Patent number
US07148220B2

Reaction notes

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