Dimethylamine → HCID 57659559, compound

HRID 217189Notes

Reaction equation

HRID 217189 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[O:29][C:28]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:30]O)[C:23]=4[CH:22]=3)[O:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH2:33][N:34](CC)[CH2:35]C.CS(Cl)(=O)=O.N(C)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][CH2:15][C:16]2[N:20]=[C:19]([C:21]3[O:29][C:28]4[CH:27]=[CH:26][N:25]=[C:24]([CH2:30][N:34]([CH3:35])[CH3:33])[C:23]=4[CH:22]=3)[O:18][N:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57659420HCID 57659420, compound

Product 1

HCID 57659559HCID 57659559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-[5-(4-hydroxymethylfuro[3,2-c]pyridine-2-yl)-[1,2,4]oxadiazole-3-ylmethoxy]piperidine-1-carboxylic acid tert-butyl ester (Example 24, 50 mg, 116 μmol) in THF was added NEt3 (50 mL, 361 μmol), followed by MsCl (15 μL, 194 μmol). After 5 min, of Me2NH (0.3 mL of a 2M solution in THF, 600 μmol) was added and stirring continued for a further 2 h. The mixture was adsorbed onto SiO2 and purified via column chromatography to give the title compound: RT=1.82 min; m/z (ES+)=458.1 [M+H]+.

Workup

  1. waitcontinued for a further 2 h
  2. custompurified via column chromatography

Sources & evidence

ORD record
ord-627a4383d67b4fa39f39fe0dcaea682f
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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