Tetrahydrofuran toluene → HCID 178486284, compound

HRID 731497Notes

Reaction equation

HRID 731497 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[S:7][C:8]([NH2:11])=[N:9][N:10]=1)(=[O:5])=[O:4].[CH:12]1([NH:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C1C[O:29][CH2:28]C1.C1(C)C=CC=CC=1>CN(C1C=CN=CC=1)C>[CH3:1][NH:2][S:3]([C:6]1[S:7][C:8]([NH:11][C:28]([N:18]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[C@H:19]2[CH2:20][CH2:21][C@H:22]([CH3:25])[CH2:23][CH2:24]2)=[O:29])=[N:9][N:10]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 22635083Tetrahydrofuran tolueneHCID 674836825-amino-N-methyl-1,3,4-thiadiazole-2-sulfonamideHCID 178461295HCID 178461295, compound

Product 1

HCID 178486284HCID 178486284, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
40 °C

Procedure

An mixture of 1,1-carbonyldiimidazole (2 equiv), 5-amino-1,3,4-thiadiazole-2-sulfonic acid methylamide, cyclohexyl-(trans-4-methyl-cyclohexyl)-amine (1 equivalent) and DMAP (5 mol %) in THF-toluene (1:1) was heated for 16 h at 40° C. and then cooled to room temperature. The reaction mixture was concentrated in vacuo and the crude product was dissolved in MeCN and purified (HPLC method 1) to give the title compound.

Workup

  1. temperaturecooled to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe crude product was dissolved in MeCN
  4. custompurified (HPLC method 1)

Sources & evidence

ORD record
ord-e75db68df4b349fabba058f0cd03c11d
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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