2-Aminothiazole → HCID 57439882, compound

HRID 2190551Notes

Reaction equation

HRID 2190551 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1.CCN=C=N[CH2:34][CH2:35][CH2:36]N(C)C.Cl.[CH3:41]N(C=O)C>CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20](=[O:21])[NH:23][C:24]3[S:25][C:26]4[CH:34]=[CH:35][CH:36]=[CH:41][C:27]=4[N:28]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27955084-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

Product 1

HCID 57439882HCID 57439882, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a mixture of 4-(4-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (250 mg, 0.82 mmol) and 2-aminothiazole (125 mg, 0.83 mmol) in DMF (20 mL) was added EDCl (184 mg, 0.96 mmol) and DMAP (100 mg, 0.83 mmol). The mixture was stirred at room temperature overnight and then heated to 100° C. for 5 hrs. Solvents were evaporated and the residue was extracted with ethyl acetate and ammonium chloride solutions. The residue was crystallized from methanol (40 mL) to afford the intermediate 4-[4-(benzothiazol-2-ylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester. LCMS calc for C23H26N4O3S (m/e) 438.17, obsd 439.2 (M+H).

Workup

  1. temperatureheated to 100° C. for 5 hrs
  2. customSolvents were evaporated
  3. extractionthe residue was extracted with ethyl acetate and ammonium chloride solutions
  4. customThe residue was crystallized from methanol (40 mL)

Sources & evidence

ORD record
ord-96a6bce66ebd4b0d980bc40e716f1274
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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