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

HRID 469035Notes

Reaction equation

HRID 469035 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]([CH2:34][N:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:30][CH2:29]1.CC(C)N=C=NC(C)C.C1C=C2N=NN(O)C2=CC=1.O>C(Cl)Cl>[CH:1]1([N:4]([CH2:18][C:19]2[O:23][CH:22]=[C:21]([C:24]([N:38]3[CH2:37][CH2:36][N:35]([CH2:34][CH:31]4[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]4)[CH2:40][CH2:39]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 27369421-((1-Methyl-4-piperidinyl)methyl)piperazineHCID 27960291-Hydroxybenzotriazole hydrateHCID 583933505-({Cyclopropyl[(4-methoxy-2,6-dimethylphenyl)sulfonyl]amino}methyl)furan-3-carboxylic acid

Product 1

HCID 58393158N-Cyclopropyl-4-methoxy-2,6-dimethyl-N-{[4-({4-[(1-methylpiperidin-4-yl)methyl]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 (126 mg, 0.33 mmol), 1-[(1-methylpiperidin-4-yl)methyl]piperazine (59 mg, 0.30 mmol), DIC (79 μL, 0.5 mmol) and HOBt monohydrate (76 mg, 0.5 mmol) in DCM (2.5 mL). The crude product was purified by FCC eluting with 95:5 DCM:7N NH3 in MeOH.

Workup

  1. customThe crude product was purified by FCC
  2. washeluting with 95:5 DCM

Sources & evidence

ORD record
ord-f00203ed808a4b9da22260b157a6b144
Source dataset
uspto-grants-2014_01
Patent number
US08623859B2

Reaction notes

Loading…