2-Thiophenecarboxaldehyde → HCID 69585891, compound

HRID 722265Notes

Reaction equation

HRID 722265 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.C([O-])(=O)C.[K+].[NH2:13][C@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C@@H:15]1[NH:23][C:24]([C:26]1[NH:27][C:28]2[C:33]([CH:34]=1)=[CH:32][C:31]([Cl:35])=[CH:30][CH:29]=2)=[O:25]>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:13][C@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C@@H:15]1[NH:23][C:24]([C:26]1[NH:27][C:28]2[C:33]([CH:34]=1)=[CH:32][C:31]([Cl:35])=[CH:30][CH:29]=2)=[O:25]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 517044Potassium AcetateHCID 58742482HCID 58742482, compound

Product 1

HCID 69585891HCID 69585891, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Thiophenecarboxaldehyde (80 μL, 0.8 mmol) and potassium acetate (90 mg, 0.9 mmol) were added to a solution of N-{(1S,2S)-1-amino-2,3-dihydro-1H-inden-2-yl}-5-chloro-1H-indole-2-carboxamide (Method 5b, 400 mg, 0.9 mmol) in MeOH (10 mL). The reaction was stirred at ambient temperature for approximately 5 mins then macroporous triethylammonium methyl polystyrene cyanoborohydride (540 mg, 0.9 mmol) was added and the reaction stirred at ambient temperature for a further 3 h. The reaction was then filtered and the volatiles were removed by evaporation under reduced pressure to afford N-{(1S,2S)-1-[(2-thienylmethyl)amino]-2,3-dihydro-1H-inden-2-yl}-5-chloro-1H-indole-2-carboxamide which was used crude in the next stage.

Workup

  1. stirringthe reaction stirred at ambient temperature for a further 3 h
  2. filtrationThe reaction was then filtered
  3. customthe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9c6a1fd2e0ad47e193ab4f7b3e6261ca
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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