Triethylamine → HCID 25006304, compound

HRID 1015419Notes

Reaction equation

HRID 1015419 reaction equation
C(N(CC)CC)C.FC(F)(F)C(O)=O.[N:15]1([CH2:21][CH2:22][O:23][C:24]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:25]=2[C:26]([NH2:35])=[N:27][C:28]([NH2:34])=[N:29]3)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[F:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43](Cl)(=[O:45])=[O:44]>O1CCCC1>[F:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43]([N:18]1[CH2:19][CH2:20][N:15]([CH2:21][CH2:22][O:23][C:24]2[CH:33]=[CH:32][CH:31]=[C:30]3[C:25]=2[C:26]([NH2:35])=[N:27][C:28]([NH2:34])=[N:29]3)[CH2:16][CH2:17]1)(=[O:45])=[O:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 67301351HCID 67301351, compound

Product 1

HCID 25006304HCID 25006304, compoundYield 310%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an 8 mL vial triethylamine (40 mg; 0.4 mmol) was added to a mixture of 5-(2-piperazin-1-yl-ethoxy)-quinazoline-2,4-diamine trifluoroacetate (50 mg; 0.1 mmol) in 1.5 mL of tetrahydrofuran. 2-Fluorobenzene-sulfonyl chloride was added and reaction stirred at room temperature for 16 hours. Reaction was purified by reprecipitation with ethanol and (0.5:1) 1N NaOH. Solids were filtered to obtain 14 mg of title compound. (310% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.77 (m, 3H), 7.48 (m, 2H), 7.32 (t, J=8.4 Hz, 1H), 7.18 (br s, 1H), 6.74 (d, J=8.4 Hz, 1H), 6.50 (d, J=7.6 Hz, 1H), 5.87 (br s, 2H), 4.16 (t, J=5.2 Hz, 2H), 3.17 (br s, 4H), 2.77 (t, J=5.2 Hz, 2H), 2.52 (m, 4H).

Workup

  1. customreaction
  2. customReaction
  3. customwas purified by reprecipitation with ethanol and (0.5:1) 1N NaOH
  4. filtrationSolids were filtered

Sources & evidence

ORD record
ord-d1e4ea95185b48a6aeb1cdc9d9233de4
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

Loading…