1,1'-Carbonyldiimidazole → HCID 178492012, compound

HRID 1244297Notes

Reaction equation

HRID 1244297 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:14][CH2:15][C:16]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)=O.O=C(C1SC=CC=1)C[NH:26][C:27]([C:29]1[S:30][C:31]2[C:37]([N:38]3[CH2:43][CH2:42][O:41][CH2:40][CH2:39]3)=[CH:36][CH:35]=[C:34]([O:44][CH3:45])[C:32]=2[N:33]=1)=O.FC(F)(F)C([O-])=O.[NH4+]>C(N(CC)CC)C>[CH3:45][O:44][C:34]1[C:32]2[N:33]=[C:29]([C:27]3[NH:14][CH:15]=[C:16]([C:18]4[S:19][CH:20]=[CH:21][CH:22]=4)[N:26]=3)[S:30][C:31]=2[C:37]([N:38]2[CH2:39][CH2:40][O:41][CH2:42][CH2:43]2)=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 2724268Ammonium trifluoroacetateHCID 126098332-Amino-1-(thiophen-2-yl)ethan-1-one hydrochlorideHCID 211370564-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-2-thiophen-2-yl-ethyl)-amide

Product 1

HCID 178492012HCID 178492012, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In accordance with scheme 2,4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (for R1=morpholinyl, XII) and CDI (1,1′-carbonyl-diimidazole) was stirred at room temperature for about 1.5 hours. Then, for example, 2-amino-1-(2-thienyl)ethanone hydrochloride (for R3=thienyl) and triethylamine were added and stirring are continued over night at room temperature. Then a mixture of the obtained 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid (2-oxo-2-thiophen-2-yl-ethyl)-amide (III) and ammonium triflouroacetate was melted at about 165° C. for 60 minutes to obtain 4-methoxy-7-morpholin-4-yl-2-(4-thiophen-2-yl-1H-imidazol-2-yl)-benzothiazole (Ia1 for R1=morpholinyl and R3=thienyl).

Workup

  1. waitare continued over night at room temperature
  2. customfor 60 minutes

Sources & evidence

ORD record
ord-d8bb2bc06f1a4a8db4b5ddfcbe2cf038
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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