Trifluoroacetic acid methylene chloride → HCID 11670392, compound

HRID 2389510Notes

Reaction equation

HRID 2389510 reaction equation
[N:1]1([C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:38][CH3:39])=[C:16]([CH:37]=2)[CH2:17][S:18][C:19]2[N:23]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[C:22]3[CH:32]=[CH:33][C:34]([F:36])=[CH:35][C:21]=3[N:20]=2)=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.ClCCl>>[N:1]1([C:10]([C:12]2[CH:13]=[CH:14][C:15]([O:38][CH3:39])=[C:16]([CH:37]=2)[CH2:17][S:18][C:19]2[N:23]([CH2:24][C:25]([OH:27])=[O:26])[C:22]3[CH:32]=[CH:33][C:34]([F:36])=[CH:35][C:21]=3[N:20]=2)=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86620039HCID 86620039, compound

Product 1

HCID 11670392HCID 11670392, compoundYield 95.2%

Procedure

tert-Butyl {2-[5-(2,3-dihydro-indole-1-carbonyl)-2-methoxy-benzylsulfanyl]-5-fluoro-benzoimidazol-1-yl}-acetate (Precursor 5-F-H-17b, 26 mg, 0.047 mmol) in a TFA/dichloromethane mixture (1:1, 0.5 ml) is allowed to stir at rt for 4 h. The solvents are removed under a stream of air. The product is precipitated in Et2O, filtered, rinsed with Et2O and dried under high vacuum. This yields the title compound (22 mg) in 99% as a light pink solid: tR=1.04 min (LC-3), ESI-MS (pos.): m/z 492.11 [M+H]+, ESI-MS (neg.): m/z 490.18 [M−H]+; 1H-NMR (DMSO-d6): δ (ppm) 2.88 (t, 2H, NCH2CH2Ar), 3.85 (t, 2H, NCH2CH2Ar), 3.89 (s, 3H, OCH3), 4.54 (s, 2H, SCH2), 4.95 (s, 2H, CH2CO2), 6.97 (t, 1Harom), 7.02-7.09 (m, 4Harom), 7.11 (d, 1Harom), 7.21 (d, 1Harom), 7.38-7.57 (m, 3Harom).

Workup

  1. customThe solvents are removed under a stream of air
  2. customThe product is precipitated in Et2O
  3. filtrationfiltered
  4. washrinsed with Et2O
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-25659dcbe4f94aa98b4bda47d46b3481
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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