Diisopropylethylamine → 4-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carbonyl]-piperazine-1-sulfonic acid dimethylamide

HRID 1818353Notes

Reaction equation

HRID 1818353 reaction equation
[CH:1]1([N:7]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:8](=[O:18])[NH:9][C:10]2[S:11][C:12]([C:15](O)=[O:16])=[CH:13][N:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[CH3:26][N:27]([CH3:37])[S:28]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)(=[O:30])=[O:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CCOC(C)=O.CN(C=O)C>[CH3:26][N:27]([CH3:37])[S:28]([N:31]1[CH2:36][CH2:35][N:34]([C:15]([C:12]2[S:11][C:10]([NH:9][C:8]([N:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])=[N:14][CH:13]=2)=[O:16])[CH2:33][CH2:32]1)(=[O:29])=[O:30]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114054472-(3,3-Dicyclohexylureido)thiazole-5-carboxylic acidHCID 22031678N,N-dimethylpiperazine-1-sulfonamide hydrochloride

Product 1

HCID 578834914-[2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carbonyl]-piperazine-1-sulfonic acid dimethylamideYield 67.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3,3-Dicyclohexyl-ureido)-thiazole-5-carboxylic acid (53 mg, 0.15 mmol), piperazine sulfonic acid dimethylamide hydrochloride (44 mg, 0.19 mmol), and HBTU (74 mg, 0.19 mmol) were weighed out and added to a 10 mL reaction flask. DMF (1.5 mL) and DIEA (65 μL, 0.38 mmol) were added. The reaction was stirred under nitrogen at ambient temperature overnight. The reaction was diluted with EtOAc (5 mL) and quenched with saturated aqueous NH4Cl (5 mL). After separation and extraction with EtOAc (2×5 mL) the combined organic portions were dried over MgSO4. Purification with silica gel (10% EtOAc and 1% MeOH in CH2Cl2) afforded 53 mg (67%) of the desired compound.

Workup

  1. additionadded to a 10 mL reaction flask
  2. customquenched with saturated aqueous NH4Cl (5 mL)
  3. customAfter separation and extraction with EtOAc (2×5 mL) the combined organic portions
  4. dry with materialwere dried over MgSO4
  5. customPurification with silica gel (10% EtOAc and 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5f41b6cf81934a1a96f9c6799a62faf3
Source dataset
uspto-grants-2009_10
Patent number
US07598391B2

Reaction notes

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