Diisopropylethylamine → (+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide

HRID 985789Notes

Reaction equation

HRID 985789 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[O:44]1[CH2:49][CH2:48][O:47][CH2:46][CH:45]1[C:50]1[C:58]2[S:57][C:56]([NH2:59])=[N:55][C:54]=2[C:53]([O:60][CH3:61])=[CH:52][CH:51]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:59][C:56]1[S:57][C:58]2[C:50]([CH:45]3[CH2:46][O:47][CH2:48][CH2:49][O:44]3)=[CH:51][CH:52]=[C:53]([O:60][CH3:61])[C:54]=2[N:55]=1)=[O:7]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2227012-Bromoisonicotinic acidHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22507697(+)-7-[1,4)Dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine

Product 1

HCID 22507693(+)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamideYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 296 mg (1.46 mmol) 2-bromo-isonicotinic acid in 10 ml THF were added 642 mg (1.69 mmol) HATU and 0.29 ml (1.69 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 1 h. 300 mg (1.13 mmol) (±)-7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-ylamine was then added and stirring continued at room temperature for 24 h. The reaction mixture was then poured into saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Trituration in ether afforded 370 mg (73%) (±)-2-bromo-N-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-isonicotinamide as a light yellow solid. ES-MS m/e (%):452 (M{81Br}+H+, 100), 450 (M{79Br}+H+, 95).

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 24 h
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-66dad1637cde4b27a1cba9696e4c8464
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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