Triethylamine → HCID 86614443, compound

HRID 1038085Notes

Reaction equation

HRID 1038085 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].C(N(CC)CC)C.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([NH:28][C:29]([C:31]4([C:58](=O)[CH3:59])[CH2:35][CH2:34][N:33]([CH2:36][C:37]([N:39]5[CH2:44][CH2:43][N:42]([C:45]6[CH:50]=[CH:49][C:48]([C:51]7[N:56]=[CH:55][CH:54]=[CH:53][N:52]=7)=[CH:47][N:46]=6)[CH2:41][CH:40]5[CH3:57])=[O:38])[CH2:32]4)=[O:30])[CH:26]=3)[NH:21][N:20]=2)=[CH:15][CH:14]=1>CO>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([NH:28][C:29]([C:31]4([C:58](=[N:4][O:2][CH3:3])[CH3:59])[CH2:35][CH2:34][N:33]([CH2:36][C:37]([N:39]5[CH2:44][CH2:43][N:42]([C:45]6[CH:50]=[CH:49][C:48]([C:51]7[N:52]=[CH:53][CH:54]=[CH:55][N:56]=7)=[CH:47][N:46]=6)[CH2:41][CH:40]5[CH3:57])=[O:38])[CH2:32]4)=[O:30])[CH:26]=3)[NH:21][N:20]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86614442HCID 86614442, compound

Product 1

HCID 86614443HCID 86614443, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Added methoxylamine hydrochloride (100 mg, 1.197 mmol) and triethylamine (0.2 ml, 1.43 mmol) to a solution of 3-Acetyl-1-{2-[2-methyl-4-(5-pyrimidin-2-yl-pyridin-2-yl)-piperazin-1-yl]-2-oxo-ethyl}-pyrrolidine-3-carboxylic acid [3-(4-fluoro-phenyl)-1H-indazol-5-yl]-amide (11N) (100 mg, 0.15 mmol) in MeOH (5 ml), then stirred for 3 hours at room temperature. The solvent was evaporated and the residue was extracted with MeCl2, washed with water, dried over Na2SO4, filtered and solvent was evaporated yielding a solid which chromatographed on silica gel eluting with 7% v/v MeOH/MeCl2 containing 2% NH4OH yielding 2 isomers:

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted with MeCl2
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customsolvent was evaporated
  7. customyielding a solid which
  8. customchromatographed on silica gel eluting with 7% v/v MeOH/MeCl2 containing 2% NH4OH yielding 2 isomers

Sources & evidence

ORD record
ord-505e1bf5fd3848d8bfd02ab6c1dd62e7
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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