Water → HCID 69212087, compound

HRID 2252056Notes

Reaction equation

HRID 2252056 reaction equation
[C:1]([Si:5]([CH3:33])([CH3:32])[O:6][CH:7]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:8]([C:10]1[CH:25]=[CH:24][C:13]2[N:14]=[C:15](Cl)[N:16]([S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[C:12]=2[CH:11]=1)=[O:9])([CH3:4])([CH3:3])[CH3:2].[CH2:34]([NH2:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O.C(Cl)Cl>C1COCC1>[CH2:34]([NH:41][C:15]1[N:16]([S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])[C:12]2[CH:11]=[C:10]([C:8](=[O:9])[CH:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:33])[CH3:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:25]=[CH:24][C:13]=2[N:14]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7504BenzylamineHCID 69208744HCID 69208744, compound

Product 1

HCID 69212087HCID 69212087, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of starting 2-(tert-butyl-dimethyl-silyloxy)-1-[2-chloro-3-(propane-2-sulfonyl)-3H-benzimidazol-5-yl]-2-phenyl-ethanone (588 mg, 1.16 mmol, 1 equiv) in 2 mL of dry THF, add benzyl amine (0.4 mL, 3.48 mmol, 3 equiv) dropwise. Heat the resulting yellow solution at 40° C. for 30 minutes, cool down to room temperature, and add water and CH2Cl2. Separate the phases and back extract the organic one with more CH2Cl2 (three times). Dry the combined organic phases over MgSO4, filter, and concentrate in vacuo to afford crude product. Purify by chromatography using CH2Cl2:hexanes (3:1) to provide the title compound (80% yield). MS(ES+): m/z=578.2 (M+H)+

Workup

  1. temperaturecool down to room temperature
  2. customSeparate the phases
  3. extractionback extract the organic one with more CH2Cl2 (three times)
  4. dry with materialDry the combined organic phases over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto afford crude product
  8. customPurify by chromatography

Sources & evidence

ORD record
ord-796ccbc34faf48778481c1874a1d7fdd
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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