Diisopropylethylamine → HCID 67258893, compound

HRID 1476668Notes

Reaction equation

HRID 1476668 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([C@@H:13]2[C@H:18]([NH2:19])[CH2:17][CH2:16][S:15][CH2:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH3:3].[CH3:20][O:21][C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](O)=[O:28])=[O:23].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([C@@H:13]2[C@H:18]([NH:19][C:27]([C:26]3[CH:25]=[C:24]([CH:32]=[CH:31][CH:30]=3)[C:22]([O:21][CH3:20])=[O:23])=[O:28])[CH2:17][CH2:16][S:15][CH2:14]2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH3:3]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 6018803-(Methoxycarbonyl)benzoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67257610HCID 67257610, compound

Product 1

HCID 67258893HCID 67258893, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (3R,4R)-3-(3-ethoxy-4-methoxyphenyl)tetrahydro-2H-thiopyran-4-amine hydrochloride (1.82 g; compound C13), 3-(methoxycarbonyl)benzoic acid (1.08 g) and HBTU (2.50 g) in DCM (50 ml) is added DIPEA (4.2 ml) and the mixture is stirred for 1 h at RT. A saturated aqueous solution of sodium hydrogen carbonate (30 ml) is added, the organic phase is separated and dried over sodium sulfate. After filtration the solvent is removed in vacuo and the resulting residue is purified by flash column chromatography [silica gel, eluation gradient: DCM/MeOH, 100/0 to 95/5 (v/v)] to give the title compound as a solid.

Workup

  1. customthe organic phase is separated
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtration the solvent
  4. customis removed in vacuo
  5. customthe resulting residue is purified by flash column chromatography [silica gel, eluation gradient: DCM/MeOH, 100/0 to 95/5 (v/v)]

Sources & evidence

ORD record
ord-d799fdae9c6d4695a59c2b16ac9e9584
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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