Diisopropylethylamine → HCID 67424859, compound

HRID 1262206Notes

Reaction equation

HRID 1262206 reaction equation
[Br:1][C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8](O)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.C1C=CC(N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O)=CC=1.[O-]S(C(F)(F)F)(=O)=O.[O:50]=[S:51]1(=[O:65])[CH2:56][CH2:55][N:54]([CH2:57][C:58]2[CH:63]=[CH:62][C:61]([NH2:64])=[CH:60][CH:59]=2)[CH2:53][CH2:52]1>CN(C)C=O.CCOC(C)=O>[Br:1][C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8]([NH:64][C:61]3[CH:62]=[CH:63][C:58]([CH2:57][N:54]4[CH2:55][CH2:56][S:51](=[O:65])(=[O:50])[CH2:52][CH2:53]4)=[CH:59][CH:60]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 142176Phenyl triflimideHCID 2758875TrifluoromethanesulfonateHCID 27796824-(4-Aminobenzyl)thiomorpholine 1,1-dioxideHCID 178517419HCID 178517419, compound

Product 1

HCID 67424859HCID 67424859, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-ol (100 mg, 0.467 mmol) was dissolved in N,N-dimethylformamide (9.00 mL) at 0° C. and N,N-diisopropylethylamine (244 μL, 1.40 mmol) was added and the reaction was let stir for 30 minutes. N-Phenylbis(trifluoromethanesulphonimide) (184 mg, 0.514 mmol) was added and the reaction was let warm to room temperature. After 100% conversion to the triflate, 4-(1,1-dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenylamine (140 mg, 0.584 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was taken up in EtOAc (30 mL) and washed three times with water (20 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-100% EtOAc/hex as the eluting solvent to obtain (7-bromo-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-[4-(1,1-dioxo-1$1(6)-thiomorpholin-4-ylmethyl)-phenyl]-amine as a yellow foam (134 mg, 66%). LCMS (m/e) 301 (M—N(CH2)4SO2); 1H-NMR (CDCl3, 400 MHz) δ 8.60 (s, 1H), 7.73 (d, 2H, J=8.5 Hz), 7.31 (d, 2H, J=8.5 Hz), 6.92 (s, 1H), 6.81 (d, 1H, J=4.8 Hz), 6.76 (d, 1H, J=4.8 Hz), 3.63 (s, 2H), 3.10-3.03 (m, 4H), 3.03-2.97 (m, 4H).

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. washwashed three times with water (20 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-8de3335eeff74bd7bd57527284f3fc38
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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