Water → 6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazole-2-carboxylic acid

HRID 538872Notes

Reaction equation

HRID 538872 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]([N:18]3[CH:22]=[CH:21][N:20]=[CH:19]3)[CH:12]([N:15]([CH3:17])[CH3:16])[CH2:13][CH3:14])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Li]C(C)(C)C.[OH2:28].C1[CH2:33][O:32]CC1>>[CH3:16][N:15]([CH3:17])[CH:12]([CH2:13][CH3:14])[CH:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:33]([OH:32])=[O:28])[S:3][C:4]=2[CH:10]=1)[N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 547620851-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethylbutan-2-amineHCID 178418306HCID 178418306, compound

Product 1

HCID 547617086-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazole-2-carboxylic acid

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-bromobenzo[d]thiazol-6-yl)-1-(1H-imidazol-1-yl)-N,N-dimethylbutan-2-amine (76 mg, 0.2 mmol) in THF (10 mL) at −78° C. was added t-BuLi (0.24 mL, 1.7 M solution) and the reaction was stirred for 15 min. Dry CO2 was bubbled for 1 h while allowing the reaction to warm to 0° C. Water was added and extracted with DCM. The water layer was neutralized and evaporated. The residue was extracted with methanol to afford 6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazole-2-carboxylic acid. MS ESI: m/Z 345.26 [M+H+].

Workup

  1. customDry CO2 was bubbled for 1 h
  2. customthe reaction
  3. extractionextracted with DCM
  4. customevaporated
  5. extractionThe residue was extracted with methanol

Sources & evidence

ORD record
ord-a201216732a04bce9f01980311d98de9
Source dataset
uspto-grants-2014_10
Patent number
US08865752B2

Reaction notes

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