(R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide → HCID 69456203, compound

HRID 1351957Notes

Reaction equation

[CH2:1]([N:3]([CH2:19][CH3:20])[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH2:15][C@H:16]([NH2:18])[CH3:17])=[CH:11][NH:12]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C@@H:35]([O:38][Si:39]([CH2:44][CH3:45])([CH2:42][CH3:43])[CH2:40][CH3:41])[CH2:36]I)=[CH:31][C:30]=1[NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:19]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH2:15][C@H:16]([NH:18][CH2:36][C@@H:35]([C:32]3[CH:33]=[CH:34][C:29]([O:28][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[C:30]([NH:46][S:47]([CH3:50])(=[O:49])=[O:48])[CH:31]=3)[O:38][Si:39]([CH2:40][CH3:41])([CH2:42][CH3:43])[CH2:44][CH3:45])[CH3:17])=[CH:11][NH:12]2)=[CH:8][CH:7]=1)=[O:5])[CH3:20]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (R)-3-(2-aminopropyl)-1H-indole-6-carboxylic acid diethylamide (20.0 mg, 0.0742 mmol) in acetonitrile (1.0 ml) is added (R)—N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]-methanesulfonamide (41.1 mg, 0.0742 mmol), and the mixture is stirred at 110° C. for 21 hours in a sealed vessel. The reaction solution is concentrated under reduced pressure, and the residue is purified by preparative TLC (a saturated ammonia solution in chloroform/methanol=50/1) to give 3-{(2R)-2-[2-(4-benzyloxy-3-methanesulfonylamino-phenyl)-(2R)-2-(triethylsilyloxy) ethylamino]propyl}-1H-indole-6-carboxylic acid diethylamide (19.2 mg, 0.0272 mmol, 37%).

Workup

concentrationThe reaction solution is concentrated under reduced pressure
customthe residue is purified by preparative TLC (a saturated ammonia solution in chloroform/methanol=50/1)

Sources & evidence

ORD record: ord-841068460b044beabb0dbd934bff8288
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217724B2

Reaction notes

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