3-Fluoro-5-(morpholin-4-yl)-N-[2-(tritylsulfanyl)benzyl]benzamide → 3-Fluoro-5-(morpholin-4-yl)-N-(2-sulfanylbenzyl)benzamide

HRID 2096248Notes

Reaction equation

HRID 2096248 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[C:36]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[CH:37]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6]>C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:35]=[C:36]([N:38]2[CH2:39][CH2:40][O:41][CH2:42][CH2:43]2)[CH:37]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[SH:15])=[O:6]

Participants

3

Reactant 1

HCID 668228043-Fluoro-5-(morpholin-4-yl)-N-[2-(tritylsulfanyl)benzyl]benzamide

Product 1

HCID 668222283-Fluoro-5-(morpholin-4-yl)-N-(2-sulfanylbenzyl)benzamideYield 72%

Reagents, catalysts & solvents 1

HCID 131726667triethylsilane TFA DCMSolvent

Procedure

3-Fluoro-5-(morpholin-4-yl)-N-[2-(tritylsulfanyl)benzyl]benzamide (517 mg, 0.88 mmol) was treated with a solution of triethylsilane/TFA/DCM (10 mL, 1/9/10). The reaction mixture was stirred at RT for 20 min and concentrated under reduced pressure. Purification of the residue by flash column chromatography (DCM:MeOH 98:2) afforded the title compound (219 mg, 72%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.36-7.31 (2H, m), 7.21-7.15 (3H, m), 6.85 (1H, ddd, J 8.5, 2.2, 1.4), 6.69 (1H, dt, J 11.6, 2.3), 6.57 (1H, br t, J 5.7), 5.39 (1H, br s), 4.66 (2H, d, J 5.7), 3.84 (4H, t, J 4.9), 3.20 (4H, t, J 4.9).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification of the residue by flash column chromatography (DCM:MeOH 98:2)

Sources & evidence

ORD record
ord-0d956430640f435b901507f750d6f3e5
Source dataset
uspto-grants-2013_05
Patent number
US08450314B2

Reaction notes

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