Dmso tfa → HCID 66834276, compound

HRID 18485Notes

Reaction equation

HRID 18485 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[C:10]([S:13][CH3:14])[CH:11]=[CH:12][C:7]=2[N:6]([C:15]([CH:17]2[CH2:22][CH:21]([CH3:23])[CH2:20][CH2:19][CH:18]2[CH:24]([CH3:26])[CH3:25])=[O:16])[C:5]1=[O:27].C(O)(C(F)(F)F)=[O:29].CS(C)=O>>[NH2:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[C:10]([S:13]([CH3:14])=[O:29])[CH:11]=[CH:12][C:7]=2[N:6]([C:15]([CH:17]2[CH2:22][CH:21]([CH3:23])[CH2:20][CH2:19][CH:18]2[CH:24]([CH3:26])[CH3:25])=[O:16])[C:5]1=[O:27]

Participants

3

Reactant 2

HCID 20405524Dmso tfaHCID 66831488HCID 66831488, compound2×

Product 1

HCID 66834276HCID 66834276, compound

Procedure

A 10 mL reaction flask was charged with 3-(2-Amino-ethyl)-1-(2-isopropyl-5-methyl-cyclohexanecarbonyl)-5-methylsulfanyl-1,3-dihydro-benzoimidazol-2-one (Compound #42, 300 mg) and 1% TFA/DMSO (1 mL). Oxygen was bubbled through the reaction mixture for 20 min and sealed. The reaction mixture was stirred for 18 h and crude product was purified by preparative HPLC (Ultro 120 (10 um) C18Q) using a 40-60% acetonitrile/H2O (with 0.1% TFA) gradient. The pure fractions were combined, concentrated and lyophilized to give a light fluffy colorless solid (296 mg 94%). MS (ESI) m/z 406 (M++1).

Workup

  1. customA 10 mL reaction flask
  2. customOxygen was bubbled through the reaction mixture for 20 min
  3. customsealed
  4. customcrude product was purified by preparative HPLC (Ultro 120 (10 um) C18Q)
  5. concentrationconcentrated
  6. customto give a light fluffy colorless solid (296 mg 94%)

Sources & evidence

ORD record
ord-6d9ecb061d284a70a07a30aabc4763ac
Source dataset
uspto-grants-2010_06
Patent number
US07741355B2

Reaction notes

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