Diisopropylethylamine → HCID 57600126, compound

HRID 1787513Notes

Reaction equation

HRID 1787513 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:22]=[CH:21][N:20]=[C:19]3[C:11]=2[C:12]2[CH:13]=[CH:14][C:15]4[C:16](=[CH:23][N:24]([CH2:26][CH2:27]OS(C)(=O)=O)[N:25]=4)[C:17]=2[S:18]3)[CH:5]=[CH:6][C:7]=1[F:8].C(N(C(C)C)CC)(C)C.[NH2:42][CH2:43][CH2:44][S:45]([CH3:48])(=[O:47])=[O:46]>CN(C=O)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:22]=[CH:21][N:20]=[C:19]3[C:11]=2[C:12]2[CH:13]=[CH:14][C:15]4[C:16](=[CH:23][N:24]([CH2:26][CH2:27][NH:42][CH2:43][CH2:44][S:45]([CH3:48])(=[O:47])=[O:46])[N:25]=4)[C:17]=2[S:18]3)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 43405612-(Methylsulfonyl)ethanamineHCID 57600141HCID 57600141, compound

Product 1

HCID 57600126HCID 57600126, compoundYield 5.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring solution of methanesulfonic acid 2-[6-(3-chloro-4-fluoro-phenylamino)-10-thia-2,3,7,9-tetraaza-cyclopenta[a]fluoren-2-yl]-ethyl ester (190 mg, 0.39 mmol) in DMF (3 mL) was added diisopropylethylamine (99 mg, 0.77 mmol) and 2-aminoethylmethylsulfone (143 mg, 1.16 mmol). It was heated to 80° C. for overnight. The crude mixture was diluted with methanol (5 mL) and it was separated by prep HPLC. The prep HPLC fractions were collected and solvent was removed by vacuum. The solid was re-dissolved by ethyl acetate (15 mL) and water (10 mL), sat. sodium carbonate solution (3 mL) was added. The organic layer was separated and dried over sodium sulfate. Evaporation of the solvents gave (3-chloro-4-fluoro-phenyl)-{2-[2-(2-methanesulfonyl-ethylamino)-ethyl]-2H-10-thia-2,3,7,9-tetraaza-cyclopenta[a]fluoren-6-yl}-amine as a white solid (10.3 mg, 5.1%) 1H-NMR (DMSO-d6) δ 9.25 (bs, 1H), 8.80 (d, 1H), 8.60 (d, 1H), 8.40 (t, 1H), 7.90 (d, 1H), 7.80 (d, 1H), 7.60 (t, 1H), 7.40 (t, 1H), 4.60 (t, 2H), 3.20 (t, 2H), 2.90 (s, 3H), 2.10 (t, 2H), 2.05 (t, 2H); LCMS RT=2.89 min; [M+H]+=519.2.

Workup

  1. customwas separated by prep HPLC
  2. customThe prep HPLC fractions were collected
  3. customsolvent was removed by vacuum
  4. dissolutionThe solid was re-dissolved by ethyl acetate (15 mL) and water (10 mL), sat. sodium carbonate solution (3 mL)
  5. additionwas added
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the solvents

Sources & evidence

ORD record
ord-1e4fb10e41914e16a08f1e8e88694bee
Source dataset
uspto-grants-2009_03
Patent number
US07511048B2

Reaction notes

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