HCID 67419236, compound → HCID 86614440, compound

HRID 1038082Notes

Reaction equation

HRID 1038082 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([CH:25]([OH:27])[CH3:26])[CH2:24][CH2:23][NH:22][CH2:21]4)=[O:19])[CH:15]=3)[N:10]([C:28]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl[CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57]2[CH:62]=[CH:61][C:60]([C:63]3[N:68]=[CH:67][CH:66]=[CH:65][N:64]=3)=[CH:59][N:58]=2)[CH2:53][CH:52]1[CH3:69])=[O:50]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]([C:20]4([CH:25]([OH:27])[CH3:26])[CH2:24][CH2:23][N:22]([CH2:48][C:49]([N:51]5[CH2:56][CH2:55][N:54]([C:57]6[CH:62]=[CH:61][C:60]([C:63]7[N:64]=[CH:65][CH:66]=[CH:67][N:68]=7)=[CH:59][N:58]=6)[CH2:53][CH:52]5[CH3:69])=[O:50])[CH2:21]4)=[O:19])[CH:15]=3)[N:10]([C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67419236HCID 67419236, compoundHCID 86614438HCID 86614438, compound

Product 1

HCID 86614440HCID 86614440, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Added N—N-Diisopropylethylamine (0.3 ml, 1.72 mmol) to a mixture of 3-(1-Hydroxy-ethyl)-pyrrolidine-3-carboxylic acid [3-(4-fluoro-phenyl)-1Trityl-indazol-5-yl]-amide (6N) (600 mg, 0.98 mmol) and 2-Chloro-1-[2-methyl-4-(5-pyrimidin-2-yl-pyridin-2-yl)-piperazin-1-yl]-ethanone (360 mg, 1.15 mmol) in DMF (10 ml) at room temperature. The solvent was evaporated and the residue extracted with MeCl2 (100 ml) and H2O (50 ml). The organic layer was separated, washed with saturated NaCl solution (20 ml), dried over MgSO4, filtered and solvent evaporated yielding 9N as a solid (750 mg, 84%) ESMS (MH, 906).

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with MeCl2 (100 ml) and H2O (50 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated NaCl solution (20 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent evaporated

Sources & evidence

ORD record
ord-238e7a9f549c4154a2a921136191e8b4
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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