Diisopropylethylamine → Phenyl 4-(4-acetylpiperazin-1-yl)-2-fluorobenzyl(cyclobutyl)sulfamate

HRID 1403724Notes

Reaction equation

HRID 1403724 reaction equation
[O-]S(C(F)(F)F)(=O)=O.C[N+]1C=CN([S:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])C=1.[CH:25]1([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([N:37]3[CH2:42][CH2:41][N:40]([C:43](=[O:45])[CH3:44])[CH2:39][CH2:38]3)=[CH:33][C:32]=2[F:46])[CH2:28][CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:43]([N:40]1[CH2:39][CH2:38][N:37]([C:34]2[CH:35]=[CH:36][C:31]([CH2:30][N:29]([CH:25]3[CH2:26][CH2:27][CH2:28]3)[S:15](=[O:17])(=[O:16])[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:32]([F:46])[CH:33]=2)[CH2:42][CH2:41]1)(=[O:45])[CH3:44]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 866906371-(4-(4-((Cyclobutylamino)methyl)-3-fluorophenyl)piperazin-1-yl)ethanoneHCID 904096313-Methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium triflate

Product 1

HCID 78210216Phenyl 4-(4-acetylpiperazin-1-yl)-2-fluorobenzyl(cyclobutyl)sulfamateYield 29.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-methyl-1-(phenoxysulfonyl)-1H-imidazol-3-ium triflate (143 mg, 0.6 mmol) and 1-(4-(4-((cyclobutylamino)methyl)-3-fluorophenyl)piperazin-1-yl)ethanone (150 mg, 0.49 mmol) in DCM (20 mL) was added diisopropylethylamine (1 mL). The mixture was stirred at ambient temperature for 16 h. After the solvent was removed, the residue was purified by prep-HPLC to provide the title compound (67.3 mg, 29.6%). 1H NMR (400 MHz, DMSO-d6) δ 7.44-7.40 (m, 2 H), 7.34-7.24 (m, 4 H), 6.79-6.67 (m, 2 H), 4.46 (s, 2 H), 4.20-4.17 (m, 1 H), 3.73-3.66 (m, 4 H), 3.26-3.17 (m, 4 H), 2.19-2.15 (m, 2 H), 2.14 (s, 3 H), 2.03-1.98 (m, 2 H), 1.62-1.52 (m, 2 H). LCMS (ESI): m/z 483.9 [M+Na+].

Workup

  1. customAfter the solvent was removed
  2. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-62839011bfdf4d03971f10d18f092aed
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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