Ethyl Acetate → HCID 69027424, compound

HRID 1433067Notes

Reaction equation

HRID 1433067 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][C:19]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:25][C:26]1[S:30][C:29]([C:31]2[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=2)=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.CCOC(C)=O>C(#N)C.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[CH:10]=[C:9]1[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH2:35][C:34]2[CH:37]=[CH:38][C:31]([C:29]3[S:30][C:26]([Cl:25])=[CH:27][CH:28]=3)=[CH:32][CH:33]=2)[CH2:20][C:19]1=[O:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 2724942TriacetoxyborohydrideHCID 534263174-(5-Chlorothiophen-2-yl)benzaldehydeHCID 544278362-(2-Oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 69027424HCID 69027424, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.10 g, 0.30 mmol) in acetonitrile (5 mL) is added 4-(5-chloro-thiophen-2-yl)-benzaldehyde (0.067 g, 0.30 mmol) followed by triacetoxyborohydride (0.13 g, 0.60 mmol) and glacial acetic acid (1 drop). The resulting mixture is stirred at room temperature overnight then poured into EtOAc and washed with water (×2) and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness then purified by column chromatography using EtOAc as the eluent to yield the title compound (0.90 g, 0.17 mmol). ESI MS [M+H]+=537.

Workup

  1. washwashed with water (×2) and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customthen purified by column chromatography

Sources & evidence

ORD record
ord-d7bee4c504c54b719c4e460c22562ef8
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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