Trifluoroacetic acid → HCID 135410954, compound

HRID 853671Notes

Reaction equation

HRID 853671 reaction equation
C([O:14][C:15]1[C:26]2[C:25](=[O:27])[N:24]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH:23](O)[C:22]=2[C:21]([O:37][CH3:38])=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[CH2:39]C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:35][C:32]1[CH:33]=[CH:34][C:29]([CH2:28][N:24]2[C:25](=[O:27])[C:26]3[C:22](=[C:21]([O:37][CH3:38])[C:20]4[N:19]=[CH:39][CH:18]=[N:17][C:16]=4[C:15]=3[OH:14])[CH2:23]2)=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58928729HCID 58928729, compound

Product 1

HCID 135410954HCID 135410954, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Benzhydryloxy-1-benzyl-6-(4-fluoro-benzyl)-7-hydroxy-8-methoxy-6,7-dihydro-1H-1,3,6-triaza-s-indacen-5-one 260 (28 mg, 0.047 mmol, 1 equiv.) was added to CH2Cl2 (1 mL) under a nitrogen atmosphere. Triethylsilane (200 μL) was added, followed by trifluoroacetic acid (200 μL). The reaction was allowed 1 hour and concentrated in vacuo until thoroughly dried. Hexanes/Ethyl ether (15 mL, 1/1 ratio) was added to the oil and sonicated. The resulting solid was then filtered and washed in Hexanes and air dried to give 7-(4-fluoro-benzyl)-5-hydroxy-9-methoxy-7,8-dihydro-pyrrolo[3,4-g]quinoxalin-6-one 261 (100%, 20 mg, 0.047 mmol) as a light gray powder. 1H NMR (300 MHz) CDCl3 δ 9.11 (bs 1 H), 7.86 (s, 1 H), 7.33-7.23 (m, 5 H), 7.01 7.07 (s, 4 H), 5.57 (s, 2 H), 4.71 (s, 2 H), 4.37 (s, 2 H), 3.57 (s, 3 H). 19F NMR (300 MHz) CDCl3 δ 62.25. MS: 418.2 (M+1)

Workup

  1. concentrationconcentrated in vacuo
  2. customuntil thoroughly dried
  3. additionHexanes/Ethyl ether (15 mL, 1/1 ratio) was added to the oil
  4. customsonicated
  5. filtrationThe resulting solid was then filtered
  6. washwashed in Hexanes
  7. customair dried

Sources & evidence

ORD record
ord-138ee9e349d74137a4ef307bcab53d42
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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