Ethanol → HCID 58717455, compound

HRID 1244769Notes

Reaction equation

HRID 1244769 reaction equation
C([N:3]([CH2:6]C)[CH2:4][CH3:5])C.N1[CH2:13][CH2:12][O:11]CC1.[ClH:14].N[C@@H:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]1O.Cl([O-])(=O)(=O)=O.[CH3:28][N+:29]1[N:33]=[CH:32][S:31]C=1SC.[CH2:36](O)[CH3:37]>>[Cl:14][C:16]1[CH:21]=[CH:20][C:19]([C:32]2[S:31][C:6](=[N:3][C@@H:4]3[CH2:5][CH2:37][CH2:36][CH2:13][C@H:12]3[OH:11])[N:29]([CH3:28])[N:33]=2)=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 702EthanolHCID 8083Morpholine2×HCID 8471TriethylamineHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-HCID 21920172HCID 21920172, compound

Product 1

HCID 58717455HCID 58717455, compound

Procedure

The compound I8 was prepared by the procedure described in Example I3 using appropriate intermediates and reagents (Protocol A). Triethylamine was replaced by morpholine resin (2.1 mmol, 0.61 g, loading 3.47 mmol/g); the mixture of morpholine resin and trans-2-aminocyclohexanol hydrochloride (2.1 mmol, 0.318 g) was stirred in ethanol (3.5 mL) at RT for 5 minutes before the addition of 3-methyl-2-methylthio[1,3,4]thiadiazolium perchlorate (3a) (0.7 mmol, 0.25 g). The residue was subjected to silica gel chromatography (Alltech column, 2 g silica) eluting with dichloromethane containing from 0% to 1% methanol. Yield: 0.050 g, 22%.

Workup

  1. customThe compound I8 was prepared by the procedure
  2. washeluting with dichloromethane containing from 0% to 1% methanol

Sources & evidence

ORD record
ord-b4392133c08c4c74a3406d694807d85d
Source dataset
uspto-grants-2006_10
Patent number
US07122565B2

Reaction notes

Loading…