Benzo(d)thiazol-2-amine → HCID 86758702, compound

HRID 2299029Notes

Reaction equation

HRID 2299029 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11](C(O)=O)[N:10]=[CH:9]1.[OH:27]N1C2C=CC=CC=2N=N1.C[CH2:38][N:39]=[C:40]=[N:41][CH2:42][CH2:43][CH2:44]N(C)C.CI.NC1[S:52][C:53]2C=CC=[CH:56][C:54]=2N=1>CN(C=O)C.C(=O)(O)[O-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:38]([NH:39][C:40]1[S:52][C:53]2[CH:54]=[CH:56][CH:44]=[CH:43][C:42]=2[N:41]=1)=[O:27]

Participants

8

Reactant 4

HCID 8706Benzo(d)thiazol-2-amineHCID 757711-HydroxybenzotriazoleHCID 10236463N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide methyliodideHCID 57016800HCID 57016800, compound

Product 1

HCID 86758702HCID 86758702, compoundYield 40.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

N-[(5S)-3-(3-Fluoro-4-(4-carboxyimidazol-1-yl)phenyl)-2-oxooxazolidin-5-ylmethyl]acetamide (1.81 g, 5 mM) and 1-hydroxybenzotriazole (0.81 g, 6 mM) were dissolved in DMF (40 ml) and stirred under nitrogen at ambient temperature. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide methiodide (1.78 g, 6 mM) was added, and the mixture stirred at ambient temperature for 2 hours, before adding 2-aminobenzothiazole (0.75 g, 5 mM). After stirring for 5 days, the mixture was diluted slowly with saturated aqueous sodium bicarbonate solution (20 ml), then water added to 250 ml. The fine precipitate was filtered, and recrystallised from a mixture of acetic acid (30 ml) and water (20 ml) to give title product (1 g).

Workup

  1. stirringthe mixture stirred at ambient temperature for 2 hours
  2. stirringAfter stirring for 5 days
  3. filtrationThe fine precipitate was filtered
  4. customrecrystallised from a mixture of acetic acid (30 ml) and water (20 ml)

Sources & evidence

ORD record
ord-fb422e4c56a948efa232c4abdf3ab0af
Source dataset
uspto-grants-2002_12
Patent number
US06495551B1

Reaction notes

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