Trimethylsilyl iodide → HCID 59829700, compound

HRID 551133Notes

Reaction equation

HRID 551133 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)[NH2:22])=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:35][C:36]1[CH:48]=[CH:47][C:39]([O:40][C:41]([CH3:46])([CH3:45])[C:42](Cl)=[O:43])=[CH:38][CH:37]=1.[Si](I)(C)(C)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([NH:22][C:42](=[O:43])[C:41]([O:40][C:39]2[CH:47]=[CH:48][C:36]([Cl:35])=[CH:37][CH:38]=2)([CH3:46])[CH3:45])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:12]1[CH:11]=[C:10]([CH2:20][CH:21]([NH:22][C:42](=[O:43])[C:41]([O:40][C:39]2[CH:47]=[CH:48][C:36]([Cl:35])=[CH:37][CH:38]=2)([CH3:46])[CH3:45])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]3[S:30][C:31]([CH3:34])=[CH:32][CH:33]=3)[CH:24]=2)[C:9]([OH:8])=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2

Participants

6

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 27813122-(4-Chlorophenoxy)-2-methylpropanoyl chlorideHCID 671714492-[8-(Benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine

Product 2

HCID 59829700HCID 59829700, compoundYield 132%HCID 67171169HCID 67171169, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-{2-(8-Benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-2-(4-chloro-phenoxy)-2-methyl-propionamide was prepared from 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine (0.409 mmol) and 2-(4-chlorophenoxy)-2-methylpropanoyl chloride (0.450 mmol, 1.1 eq.) according to the general procedure described above (Alternate General Procedure for N-Acylations). Ethyl acetate was used in place of dichloromethane in the workup procedure. Crude product obtained was a tan solid that was subjected to the conditions described above for TMSI-mediated O-benzyl deprotection. Crude product from the deprotection was a brown solid that was purified by column chromatography using 5% methanol/dichloromethane to give the title compound as a white solid (0.270 mmol, 66% for 2 steps). MS (ESI) m/z 591.4.

Workup

  1. customCrude product obtained
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d7597b32260d47d89870a18bf1f8c45c
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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