Methanesulfonamide → HCID 72549136, compound

HRID 1849890Notes

Reaction equation

HRID 1849890 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:35])[CH2:21][C:22]2[C:30]([CH:31]3[CH2:33][CH2:32]3)=[CH:29][C:25]([C:26]([OH:28])=O)=[C:24]([F:34])[CH:23]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][S:37]([NH2:40])(=[O:39])=[O:38].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH:1]([N:14]1[CH2:15][CH2:16][N:17]([C:20](=[O:35])[CH2:21][C:22]2[C:30]([CH:31]3[CH2:33][CH2:32]3)=[CH:29][C:25]([C:26]([NH:40][S:37]([CH3:36])(=[O:39])=[O:38])=[O:28])=[C:24]([F:34])[CH:23]=2)[CH2:18][CH2:19]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86703769HCID 86703769, compound

Product 1

HCID 72549136HCID 72549136, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-(2-(4-benzhydrylpiperazin-1-yl)-2-oxoethyl)-5-cyclopropyl-2-fluorobenzoic acid (35 mg, 0.074 mmol), methanesulfonamide (11 mg, 0.11 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (28 mg, 0.15 mmol) and 4-dimethylaminopyridine (18 mg, 0.15 mmol) in dichloromethane (2 mL) was stirred at room temperature for 16 h. The mixture was diluted with DCM (10 mL), washed with HCl (2M, 8 mL) and brine (8 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Combiflash (30%-40% CH3CN in 0.1% NH4HCO3) to afford target compound (5 mg, 12.3%) as a white solid. LCMS (ESI) Method A: RT=5.17 min, m/z: 550.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6): δ 7.44-7.43 (m, 4H), 7.31-7.26 (m, 5H), 7.21-7.18 (m, 2H), 6.82 (d, J=11.0 Hz, 1H), 4.34 (s, 1H), 3.81 (s, 2H), 3.53 (brs, 4H), 2.88 (s, 3H), 2.28 (brs, 4H), 1.76-1.75 (m, 1H), 0.83-0.81 (m, 2H), 0.51-0.49 (m, 2H).

Workup

  1. washwashed with HCl (2M, 8 mL) and brine (8 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by Combiflash (30%-40% CH3CN in 0.1% NH4HCO3)

Sources & evidence

ORD record
ord-68aa69aefc9440ebbb5b89b06cfd491b
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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