Water → HCID 57471284, compound

HRID 510530Notes

Reaction equation

HRID 510530 reaction equation
[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[C:10]2[CH:9]=[C:8]([OH:21])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.Br[CH2:23][CH:24]([F:28])[CH2:25][CH2:26]Br.C(N(CC)CC)C.O>C(#N)C.C(OC(=O)C)C>[Cl:20][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[Cl:19])[CH2:12][CH:11]1[C:10]2[CH:9]=[C:8]([OH:21])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH:2]1[N:1]1[CH2:26][CH2:25][CH:24]([F:28])[CH2:23]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 57471196HCID 57471196, compoundHCID 57471283112464-88-7

Product 1

HCID 57471284HCID 57471284, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Amino-8-(3,4-dichlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-ol (691 mg, 2.146 mmol, example 34), 2 eq of 1,4-dibromo-2-fluorobutane, and 3 eq of triethylamine were dissolved in acetonitrile (10 ml) and heated in the microwave for 2 h. Addition of water with ethylacetate, washing of the organic phase with saturated NaHCO3, NaCl, drying over Na2SO4 and flash chromatography (silica gel, CH2Cl2/MeOH 95:5) gave 8-(3,4-dichlorobenzyl)-7-(3-fluoropyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-ol (330 mg, 39%). The ethylene sulfonamide side chain was added in analogy to examples 1, 7, 8 to give 1-cyclopropyl-N-[2-({8-(3,4-dichlorobenzyl)-7-[3-fluoropyrrolidin-1-yl]-5,6,7,8-tetrahydronaphthalen-2-yl}oxy)ethyl]methanesulfonamide.

Workup

  1. temperatureheated in the microwave for 2 h
  2. washwashing of the organic phase with saturated NaHCO3, NaCl
  3. dry with materialdrying over Na2SO4 and flash chromatography (silica gel, CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-ac52d3524d0243b9b704a9f29ec42b8d
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

Loading…