Diisopropylethylamine → HCID 68878477, compound

HRID 493170Notes

Reaction equation

HRID 493170 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[O:18][C:17]([C:19]([OH:21])=O)=[CH:16][C:15]=3[CH:22]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[NH:23]1[CH2:28][CH2:27][S:26](=[O:30])(=[O:29])[CH2:25][CH2:24]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>C1COCC1>[O:29]=[S:26]1(=[O:30])[CH2:27][CH2:28][N:23]([C:19]([C:17]2[O:18][C:14]3[CH:13]=[CH:12][C:11]([O:10][CH:7]4[CH2:8][CH2:9][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:5][CH2:6]4)=[CH:22][C:15]=3[CH:16]=2)=[O:21])[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6484228Thiomorpholine 1,1-dioxideHCID 68724847HCID 68724847, compound

Product 1

HCID 68878477HCID 68878477, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a flask were mixed together the above prepared 5-(1-isopropyl-piperidin-4-yloxy)-benzofuran-2-carboxylic acid (1.25 g, 3.92 mmol, calculated as 73%), thiomorpholine 1,1-dioxide (0.636 g, 1.2 eq.), (benzotriazol-1-yloxy)-tris-(dimethylamino)phosphonium hexafluorophosphate (2.081 g, 1.2 eq.) and 2.4 eq. of N-ethyldiisopropylamine (1.60 mL) in 24 mL of abs. THF and allowed to react during one night at ambient temperature. Pouring onto crashed ice/AcOEt/NH4Cl-solution, twofold extraction with AcOEt, washing with water and brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, NEt3/AcOEt=2/98) and trituration in hexane/AcOEt=7/3 yielded 1.192 g of the title compound as off-white crystals.

Workup

  1. additionIn a flask were mixed together the
  2. customto react during one night at ambient temperature
  3. additionPouring
  4. extractionextraction with AcOEt
  5. washwashing with water and brine
  6. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-7200448fdf344938a400e5bac6a72bb1
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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