Water → HCID 67444143, compound

HRID 1400891Notes

Reaction equation

HRID 1400891 reaction equation
Cl.Cl.[CH:3]1([NH:6][C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[CH:23]=[C:24]([C:26]5[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=5)[S:25][C:18]=34)=[C:12]([F:32])[CH:11]=2)=[O:8])[CH2:5][CH2:4]1.CCN([CH:39]([CH3:41])[CH3:40])C(C)C.CC(C[C:48](Cl)=[O:49])C(Cl)=O.[OH2:51].CN([CH:55]=[O:56])C>>[CH:3]1([NH:6][C:7](=[O:8])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]4[CH:23]=[C:24]([C:26]5[CH2:27][CH2:28][N:29]([C:48](=[O:49])[CH2:41][CH2:39][C:40]([O:56][CH3:55])=[O:51])[CH2:30][CH:31]=5)[S:25][C:18]=34)=[C:12]([F:32])[CH:11]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 125139702-Methylbutanedioyl dichlorideHCID 67442257HCID 67442257, compound

Product 1

HCID 67444143HCID 67444143, compoundYield 63%

Procedure

To a stirred suspension of 271 (150 mg, 0.302 mmol) and DIPEA (123 μL, 0.707 mmol) in DMF (10 mL) was added methyl succinyl chloride (65 μl, 0.53 mmol). The reaction mixture was stirred at RT for 2.5 days. Water was added and the reaction mixture was extracted with DCM. The organic layer was successively washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Biotage (SNAP 80 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20 CV), to afford the title compound 272 (120 mg, 0.223 mmol, 63% yield) as an off-white solid. MS (m/z): 539.5 (M+H).

Workup

  1. extractionthe reaction mixture was extracted with DCM
  2. washThe organic layer was successively washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by Biotage (SNAP 80 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20 CV)

Sources & evidence

ORD record
ord-eef320b5026440cc8376f2f4bafc0b33
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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