Diethylamine → HCID 57852692, compound

HRID 1890146Notes

Reaction equation

HRID 1890146 reaction equation
[CH:1]1[C:6]2[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH:16]([C:18]([OH:20])=O)[S:17][C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:13][CH:12]=[CH:11][CH:10]=4.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:21]([N:23]([CH2:24][CH3:25])[C:18]([CH:16]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:17]1)=[O:20])[CH3:22]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 15886891HCID 15886891, compound

Product 1

HCID 57852692HCID 57852692, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 6,11-dihydro-5-thia-11-aza-benzo[α]fluorene-6-carboxylic acid (1.65 g, 6 mmol) in CH2Cl2 (15 ml) were added diethylamine (0.7 ml, 7 mmol), bromotripyrrolidinophosphonium hexafluorophosphate (2.75 g, 6 mmol) and diisopropylethylamine (3.1 ml, 18 mmol). The reaction was stirred at room temperature for 3 days. The reaction mixture was diluted with CH2Cl2 (100 ml), washed with 1N HCl, saturated NaHCO3 soln, brine, dried (MgSO4) and evaporated. The residue was purified by silica gel chromatography eluting with 50% EtOAc/petroleum ether to give 1.07 g (54%) of 6,11-dihydro-5-thia-11-aza-benzo[α]fluorene-6-carboxylic acid diethylamide as a yellow solid. 1H NMR (CDCl3) δ 9.23 (1H, s), 7.33 (1H, dd), 7.20 (1H, dd), 7.69-7.08 (5H, m), 6.66-6.72 (1H, m), 5.33 (1H, s), 3.34-3.76 (4H, m), 1.39 (3H, t), 1.37 (3H, t).

Workup

  1. washwashed with 1N HCl, saturated NaHCO3 soln
  2. dry with materialbrine, dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 50% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-00116c19019848bb9bf55113dad07b62
Source dataset
uspto-grants-2013_08
Patent number
US08506932B2

Reaction notes

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