HCID 86614441, compound → HCID 86614442, compound

HRID 1038084Notes

Reaction equation

HRID 1038084 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4([C:47](=[O:49])[CH3:48])[CH2:24][CH2:23][N:22]([CH2:25][C:26]([N:28]5[CH2:33][CH2:32][N:31]([C:34]6[CH:39]=[CH:38][C:37]([C:40]7[N:45]=[CH:44][CH:43]=[CH:42][N:41]=7)=[CH:36][N:35]=6)[CH2:30][CH:29]5[CH3:46])=[O:27])[CH2:21]4)=[O:19])[CH:15]=3)[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4([C:47](=[O:49])[CH3:48])[CH2:24][CH2:23][N:22]([CH2:25][C:26]([N:28]5[CH2:33][CH2:32][N:31]([C:34]6[CH:39]=[CH:38][C:37]([C:40]7[N:41]=[CH:42][CH:43]=[CH:44][N:45]=7)=[CH:36][N:35]=6)[CH2:30][CH:29]5[CH3:46])=[O:27])[CH2:21]4)=[O:19])[CH:15]=3)[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86614441HCID 86614441, compound

Product 1

HCID 86614442HCID 86614442, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Stirred 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)-1Trityl-indazol-5-yl]-amide (10N) (600 mg, 0.664 mmol) in trifluoroacetic acid (20 ml) at room temperature overnight. The solvent was evaporated, water (100 ml) and 1N NaOH (10 ml) were added. The mixture was extracted with MeCl2 (2×150 ml), dried over MgSO4, filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with 10% v/v MeOH/MeCl2 containing 2% NH4OH yielding product as a white solid. (350 mg, 79%) LCMS (MH 662.4). Retention time (minutes) 2.21

Workup

  1. customThe solvent was evaporated
  2. additionwater (100 ml) and 1N NaOH (10 ml) were added
  3. extractionThe mixture was extracted with MeCl2 (2×150 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customyielding a residue which
  8. customchromatographed on silica gel eluting with 10% v/v MeOH/MeCl2 containing 2% NH4OH yielding product as a white solid

Sources & evidence

ORD record
ord-55c86552c38c4f188fe18a7557f5fa81
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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