Diisopropylethylamine → HCID 68228371, compound

HRID 1521871Notes

Reaction equation

HRID 1521871 reaction equation
[N:1]1([C:7]([C:9]2[C:10]3[CH2:27][S:26](=[O:29])(=[O:28])[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:11]=3[N:12]([CH:14]3[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]3)[N:13]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[O:39]1[CH:43]=[CH:42][C:41]([C:44](Cl)=[O:45])=[CH:40]1>C(Cl)Cl>[O:39]1[CH:43]=[CH:42][C:41]([C:44]([N:16]2[CH2:17][CH2:18][CH2:19][CH:14]([N:12]3[C:11]4[C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=5[S:26](=[O:29])(=[O:28])[CH2:27][C:10]=4[C:9]([C:7]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:8])=[N:13]3)[CH2:15]2)=[O:45])=[CH:40]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27761233-Furoyl chlorideHCID 66578828HCID 66578828, compound

Product 1

HCID 68228371HCID 68228371, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Enantiomer B of 3-(morpholin-4-ylcarbonyl)-1-[piperidin-3-yl]-1,4-dihydrothiochromeno[4,3-c]pyrazole 5,5-dioxide (30 mg; 0.07 mmol; 1 eq.) in DCM (0.45 mL) is added N,N-diisopropylethylamine (25 μl; 0.14 mmol; 2 eq.) followed by 3-furoyl chloride (14 mg; 0.11 mmol; 1.5 eq.) and the reaction mixture is stirred at rt overnight. The solvent is concentrated and the residue is purified by flash chromatography (eluent MeOH/EtOAc 0 to 10%) to afford 20 mg (54%) of the title compound as a white foam. 1H NMR (DMSO-d6): δ 8.04 (d, J=7.7 Hz, 2H), 7.86 (s, 1H), 7.75 (d, J=7.8 Hz, 2H), 6.67 (s, 1H), 4.85 (s, 1H), 4.79 (s, 2H), 3.91 (s, 2H), 3.64 (d, J=9.7 Hz, 5H), 2.26 (s, 2H), 1.95-1.61 (m, 2H). HPLC (max plot) 99.4%; Rt 3.02 min. MS (ESI+): 511.30.

Workup

  1. concentrationThe solvent is concentrated
  2. customthe residue is purified by flash chromatography (eluent MeOH/EtOAc 0 to 10%)

Sources & evidence

ORD record
ord-3f2b00f57bd6426e85255fbdc84a18be
Source dataset
uspto-grants-2015_07
Patent number
US09073940B2

Reaction notes

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