Diisopropylcarbodiimide → N-cyclopropyl-4-methoxy-2,6-dimethyl-N-[(4-{[4-(1-methylpiperidin-4-yl)piperazin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

HRID 469026Notes

Reaction equation

HRID 469026 reaction equation
[CH:1]1([N:4]([CH2:18][C:19]2[O:23][CH:22]=[C:21]([C:24](O)=[O:25])[CH:20]=2)[S:5]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=2[CH3:17])(=[O:7])=[O:6])[CH2:3][CH2:2]1.[CH3:27][N:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:30][CH2:29]1.CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH:1]1([N:4]([CH2:18][C:19]2[O:23][CH:22]=[C:21]([C:24]([N:37]3[CH2:36][CH2:35][N:34]([CH:31]4[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]4)[CH2:39][CH2:38]3)=[O:25])[CH:20]=2)[S:5]([C:8]2[C:9]([CH3:17])=[CH:10][C:11]([O:15][CH3:16])=[CH:12][C:13]=2[CH3:14])(=[O:6])=[O:7])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 583933505-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)furan-3-carboxylic acid

Product 1

HCID 46176076N-cyclopropyl-4-methoxy-2,6-dimethyl-N-[(4-{[4-(1-methylpiperidin-4-yl)piperazin-1-yl]carbonyl}furan-2-yl)methyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared according to general procedure AM using 5-({cyclopropyl[(4-methoxy-2,6 dimethylphenyl)sulfonyl]amino}methyl)furan-3-carboxylic acid (47 mg, 0.12 mmol), 1-(1-methylpiperidin-4-yl)piperazine (21 mg, 0.11 mmol), DIC (0.3 mL, 1.87 mmol), HOBt (29 mg, 0.19 mmol) and TEA (0.07 mL, 0.48 mmol) in DCM (5 mL). The crude product was purified using Isolute SCX-2 cartridge, washing with MeOH (3 mL) and eluting with 7N NH3 in MeOH (3 mL) to afford the title compound.

Workup

  1. customThe title compound was prepared
  2. customThe crude product was purified
  3. washwashing with MeOH (3 mL)
  4. washeluting with 7N NH3 in MeOH (3 mL)

Sources & evidence

ORD record
ord-c6417f2c252543ef804a669e297c95d9
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

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