Diisopropylethylamine → Ammonia

HRID 1351931Notes

Reaction equation

HRID 1351931 reaction equation
[NH2:1][C@H:2]([CH3:22])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][CH2:14][C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[F:23][C:24]([F:29])([F:28])[C:25]([O-:27])=[O:26].[Cl:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C@H:34]1[O:36][CH2:35]1.[CH3:40][CH2:41][N:42](C(C)C)C(C)C>C(#N)C>[NH3:1].[F:23][C:24]([F:29])([F:28])[C:25]([OH:27])=[O:26].[OH2:13].[C:41](#[N:42])[CH3:40].[Cl:30][C:31]1[CH:32]=[C:33]([C@@H:34]([OH:36])[CH2:35][NH:1][C@H:2]([CH3:22])[CH2:3][C:4]2[C:12]3[C:7](=[C:8]([O:13][CH2:14][C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[O:16])[CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)[CH:37]=[CH:38][CH:39]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 69456022(R)-N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide

Product 3

HCID 222AmmoniaHCID 22145617Water TFA acetonitrileHCID 69711432N-[2-(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indol-7-yloxy)acetyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)—N-{2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-acetyl}methanesulfonamide.trifluoroacetate (40 mg, 0.091 mmol), (R)-(+)-3-chlorostyrene oxide (24 μL, 0.18 mmol) and iPr2NEt (24 μL, 0.137 mmol) in acetonitrile (1 mL) is refluxed for 8 hours. After cooling, the mixture is concentrated and purified by preparative TLC (thickness: 0.5 mm, methanol/(a saturated ammonia solution in chloroform)=1/3) and preparative reversed phase HPLC (trifluoroacetic acid/water/acetonitrile) to give the desired N-[2-(3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indol-7-yloxy)acetyl]methanesulfonamide.trifluoroacetate (9 mg, yield: 21%).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. custompurified by preparative TLC (thickness

Sources & evidence

ORD record
ord-0d8bc8888b8f4aea92e04bb75b135104
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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