Diisopropylethylamine → HCID 69457519, compound

HRID 1351968Notes

Reaction equation

HRID 1351968 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:16]I)=[CH:11][C:10]=1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:31][C@H:32]([CH3:47])[CH2:33][C:34]1[C:42]2[C:37](=[C:38]([C:43]([O:45][CH3:46])=[O:44])[CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>O1CCCC1.C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si:19]([CH2:24][CH3:25])([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:16][NH:31][C@H:32]([CH3:47])[CH2:33][C:34]2[C:42]3[C:37](=[C:38]([C:43]([O:45][CH3:46])=[O:44])[CH:39]=[CH:40][CH:41]=3)[NH:36][CH:35]=2)=[CH:11][C:10]=1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 54211801(R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamideHCID 86604025HCID 86604025, compound

Product 1

HCID 69457519HCID 69457519, compoundYield 42.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxy-ethyl)phenyl]methanesulfonamide (2.09 g, 3.72 mmol), methyl (R)-3-(2-aminopropyl)-1H-indole-7-carboxylate (1.00 g, 3.72 mmol), diisopropyl-ethylamine (1.9 ml, 11.2 mmol) in tetrahydrofuran (30 ml)-acetonitrile (20 ml) is stirred at 110° C. for 18 hours in a sealed vessel. After cooling, to the reaction solution are added a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, and the mixture is extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (chloroform/methanol=100/1→100/4) to give the title compound (1.05 g, yield: 42%).

Workup

  1. temperatureAfter cooling, to the reaction solution
  2. extractiona saturated brine, and the mixture is extracted with ethyl acetate
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (chloroform/methanol=100/1→100/4)

Sources & evidence

ORD record
ord-102a6d88d6c149acb81f25760ed43f90
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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