Triethylamine → 2-(Benzyloxy)-N-{2-(5-chloro-8-hydroxyquinolin-7-yl)-1-[3-(5-methyl-2-thienyl)phenyl]ethyl}acetamide

HRID 551132Notes

Reaction equation

HRID 551132 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.[CH2:35]([O:42][CH2:43][C:44](Cl)=[O:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)CC)C.[Si](I)(C)(C)C>C(OCC)(=O)C>[CH2:35]([O:42][CH2:43][C:44]([NH:22][CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[S:30][C:31]([CH3:34])=[CH:32][CH:33]=2)[CH:24]=1)[CH2:20][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[N:17]2)=[C:12]([Cl:19])[CH:11]=1)=[O:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[CH2:35]([O:42][CH2:43][C:44]([NH:22][CH:21]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[S:30][C:31]([CH3:34])=[CH:32][CH:33]=2)[CH:24]=1)[CH2:20][C:10]1[C:9]([OH:8])=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[N:17]2)=[C:12]([Cl:19])[CH:11]=1)=[O:45])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 85247Trimethylsilyl iodideHCID 177085Benzyloxyacetyl chloride2×HCID 671714492-[8-(Benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine

Product 2

HCID 598296992-(Benzyloxy)-N-{2-(5-chloro-8-hydroxyquinolin-7-yl)-1-[3-(5-methyl-2-thienyl)phenyl]ethyl}acetamideYield 57.4%HCID 671710812-Benzyloxy-N-{2-(8-benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Benzyloxy-N-{2-(8-benzyloxy-5-chloro-quinolin-7-yl)-1-[3-(5-methyl-thiophen-2-yl)-phenyl]-ethyl}-acetamide was prepared from 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanamine (0.411 mmol) and benzyloxyacetyl chloride (0.452 mmol, 1.1 eq.) according to the general procedure described above (Alternate General Procedure for N-Acylations). After stirring 15 min at room temperature, additional benzyloxyacetyl chloride (0.206 mmol, 0.5 eq.) and triethylamine (0.206 mmol, 0.5 eq.) was added. Stirring was continued for 2 min at room temperature and the reaction was worked up as described in the general procedure. Ethyl acetate was used in place of dichloromethane in the workup procedure. Crude product obtained was a white foam that was subjected to the conditions described above for TMSI-mediated O-benzyl deprotection. Crude product obtained was a brown solid that was purified by column chromatography using 10% acetone/dichloromethane to give the title compound as a tan solid (0.118 mmol, 29% for 2 steps). MS (ESI) m/z 543.4.

Workup

  1. stirringStirring
  2. waitwas continued for 2 min at room temperature
  3. customCrude product obtained
  4. customCrude product obtained
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c8ced9e0745144d8b59cdf47cd336068
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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