Ethyl chloroformate → Ethyl (6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamate

HRID 538868Notes

Reaction equation

HRID 538868 reaction equation
[CH3:1][N:2]([CH3:22])[CH:3]([CH2:20][CH3:21])[CH:4]([C:10]1[CH:19]=[CH:18][C:13]2[N:14]=[C:15]([NH2:17])[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.CCN(C(C)C)C(C)C.Cl[C:33]([O:35][CH2:36][CH3:37])=[O:34]>C(Cl)Cl.CC(O)=O.C1COCC1>[CH3:1][N:2]([CH3:22])[CH:3]([CH2:20][CH3:21])[CH:4]([C:10]1[CH:19]=[CH:18][C:13]2[N:14]=[C:15]([NH:17][C:33](=[O:34])[O:35][CH2:36][CH3:37])[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 547593306-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine

Product 1

HCID 54761887Ethyl (6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 23444217Acetic acid tetrahydrofuranSolvent

Procedure

A solution of 6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-amine (52 mg, 0.16 mmol) and Hunig's base (31.6 μL, 0.18 mmol) in DCM (1 mL) was treated with ethyl chloroformate (17.3 μL, 0.0.18 mmol) in 2 mL 10% AcOH THF. The mixture was stirred at room temperature overnight. The solution was concentrated in vacuo and the residue was purified using PTLC on a 1 mm silica plate eluting with 5% MeOH (2N NH3)/DCM to provide Ethyl (6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)carbamate. MS (ESI+) m/z 388.17 [M+H]+

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified
  3. washeluting with 5% MeOH (2N NH3)/DCM

Sources & evidence

ORD record
ord-c2539dce05b74661bbc07bee338b6f88
Source dataset
uspto-grants-2014_10
Patent number
US08865752B2

Reaction notes

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