Trifluoroacetic acid → HCID 9924505, compound

HRID 1582450Notes

Reaction equation

HRID 1582450 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:27])[C:11](=O)[C:12]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:13]=23)=[CH:5][CH:4]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>ClCCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:27])[CH2:11][C:12]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:13]=23)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 9968992HCID 9968992, compound

Product 1

HCID 9924505HCID 9924505, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(Chart C, Step 1): A solution of N-(4-methoxyphenyl)-2-oxo-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide (355 mg, 0.98 mmol) in 1,2-dichloroethane (20 mL) is treated with TFA (2.5 mL) and triethylsilane (2.5 mL). The resulting clear golden solution is heated to reflux. After 18 hrs, the reaction is cooled to rt, washed twice with saturated sodium bicarbonate (50 mL), once with brine (50 mL), dried over MgSO4, filtered, and concentrated to give a golden oil. This material is purified by LC (230-400 silica gel) eluting with 5:0.5:94.5 methanol/NH4OH/dichloromethane to afford 275 mg of N-(4-methoxyphenyl)-2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)acetamide as a white foam. IR (drift) 1662, 1602, 1535, 1512, 1467, 1411, 1372, 1358, 1323, 1297, 1243, 1180, 1032, 830, 740 cm−1; OAMS supporting ions at: ESI+350.2.

Workup

  1. temperatureThe resulting clear golden solution is heated to reflux
  2. washwashed twice with saturated sodium bicarbonate (50 mL), once with brine (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a golden oil
  7. customThis material is purified by LC (230-400 silica gel)
  8. washeluting with 5:0.5:94.5 methanol/NH4OH/dichloromethane

Sources & evidence

ORD record
ord-1e6a9626d5454b598489ccff4e2477d6
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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