Dimethyl Sulfoxide → HCID 86614441, compound

HRID 1038083Notes

Reaction equation

HRID 1038083 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([NH:27][C:28]([C:30]4([CH:57]([OH:59])[CH3:58])[CH2:34][CH2:33][N:32]([CH2:35][C:36]([N:38]5[CH2:43][CH2:42][N:41]([C:44]6[CH:49]=[CH:48][C:47]([C:50]7[N:55]=[CH:54][CH:53]=[CH:52][N:51]=7)=[CH:46][N:45]=6)[CH2:40][CH:39]5[CH3:56])=[O:37])[CH2:31]4)=[O:29])[CH:25]=3)[N:20]([C:60]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[N:19]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.O>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([NH:27][C:28]([C:30]4([C:57](=[O:59])[CH3:58])[CH2:34][CH2:33][N:32]([CH2:35][C:36]([N:38]5[CH2:43][CH2:42][N:41]([C:44]6[CH:49]=[CH:48][C:47]([C:50]7[N:51]=[CH:52][CH:53]=[CH:54][N:55]=7)=[CH:46][N:45]=6)[CH2:40][CH:39]5[CH3:56])=[O:37])[CH2:31]4)=[O:29])[CH:25]=3)[N:20]([C:60]([C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)[C:67]3[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=3)[N:19]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86614440HCID 86614440, compound

Product 1

HCID 86614441HCID 86614441, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

Added DMSO (200 mg, 2.56 mmol) to a solution of oxalyl chloride (180 mg, 1.40 mmol) in MeCl2 (10 ml) at −78° C., then stirred at −78° C. for 1 hour. Added 3-(1-Hydroxy-ethyl)-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 (9N) in MeCl2 (5 ml) at −78° C. then stirred at −78° C. for 2 hours. Triethylamine (200 mg, 1.96 mmol) was added, the solution allowed warm to room temperature then stirred overnight. Added water (50 ml) and MeCl2 (150 ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding 10N as a solid (600 mg, 66%) ESMS (MH, 904)

Workup

  1. temperaturethe solution allowed warm to room temperature
  2. stirringthen stirred overnight
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvent evaporated

Sources & evidence

ORD record
ord-54f12418fb1346a4bcc67553895e35e9
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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