HCID 131729956, compound → HCID 70696660, compound

HRID 2389506Notes

Reaction equation

HRID 2389506 reaction equation
C([O:5][C:6](=[O:32])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH:17]=[O:18])=[CH:16][C:11]=2[N:10]=[C:9]1[S:19][CH2:20][C:21]1[CH:26]=[C:25]([C:27](=[O:29])[CH3:28])[CH:24]=[CH:23][C:22]=1[O:30][CH3:31])(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[C:27]([C:25]1[CH:24]=[CH:23][C:22]([O:30][CH3:31])=[C:21]([CH:26]=1)[CH2:20][S:19][C:9]1[N:8]([CH2:7][C:6]([OH:32])=[O:5])[C:12]2[CH:13]=[CH:14][C:15]([CH:17]=[O:18])=[CH:16][C:11]=2[N:10]=1)(=[O:29])[CH3:28]

Participants

3

Reactant 1

HCID 131729956HCID 131729956, compound

Product 1

HCID 70696660HCID 70696660, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of tert-butyl[2-(5-acetyl-2-methoxy-benzylsulfanyl)-5-formyl-benzoimidazol-1-yl]-acetate (Precursor 5-HCO—H-11b, 16 mg, 0.035 mmol) in TFA/dichloromethane (1:1, 4 ml) is allowed to stir overnight at rt. The solvents are removed under a stream of air and the resulting products are dried under high vacuum. This yields the title compound (14 mg) in 100% as a yellow solid: tR=0.94 min (LC-3), ESI-MS (pos.): m/z 398.86 [M+H]+, ESI-MS (neg.): m/z 397.06 [M−H]+; 1H-NMR (DMSO-d6): δ (ppm) 2.46 (s, 3H, COCH3), 3.88 (s, 3H, OCH3), 4.59 (s, 2H, SCH2), 4.96 (s, 2H, CH2CO2), 7.11 (d, 1Harom), 7.65 (d, 1Harom), 7.74 (d, 1Harom), 7.90 (dd, 1Harom), 8.06 (d, 1Harom), 8.12 (d, 1Harom), 10.01 (s, 1H, CHO).

Workup

  1. customThe solvents are removed under a stream of air
  2. customthe resulting products are dried under high vacuum

Sources & evidence

ORD record
ord-6e845facbd9d4b8d850bf2a28e165b06
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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