Hydrochloric Acid → HCID 57487110, compound

HRID 1044507Notes

Reaction equation

HRID 1044507 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][NH2:19])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.[CH:29]1([S:33](Cl)(=[O:35])=[O:34])[CH2:32][CH2:31][CH2:30]1.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:5][CH:6]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][CH2:18][NH:19][S:33]([CH:29]3[CH2:32][CH2:31][CH2:30]3)(=[O:35])=[O:34])[CH:12]=[CH:11][C:10]=2[CH2:9][CH2:8][CH:7]1[N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 22636930Cyclobutanesulfonyl chlorideHCID 57471235HCID 57471235, compound

Product 1

HCID 57487110HCID 57487110, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(8-(3,4-Dichlorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-yloxy)ethanamine (120 mg, 0.286 mmol), para-(N,N-dimethylamino) pyridine (1.40 g, 19.7 mmol), and cyclobutanesulfonyl chloride (46.5 mg, 0.30 mmol) were dissolved in CH2Cl2 (20 ml) and stirred for 14 h at room temperature. 0.5N HCl was added, the organic phase separated and the aqueous phase extracted with CH2Cl2. The combined organic layers were washed with water, NaHCO3 solution, and saturated NaCl solution, dried over Na2SO4, and concentrated to afford a residue that was purified by flash chromatography (silica gel, MeOH/CH2Cl2 3:97→5:95). The white solid product (164 mg, 32%) was trans-ferred to an HCl salt and precipitated from diisopropyl ether.

Workup

  1. customthe organic phase separated
  2. extractionthe aqueous phase extracted with CH2Cl2
  3. washThe combined organic layers were washed with water, NaHCO3 solution, and saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford a residue that
  7. customwas purified by flash chromatography (silica gel, MeOH/CH2Cl2 3:97→5:95)
  8. customprecipitated from diisopropyl ether

Sources & evidence

ORD record
ord-054711f465244e5a8ed03f11c52393cb
Source dataset
uspto-grants-2013_10
Patent number
US08563617B2

Reaction notes

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