Acetic Acid → N-{3-Cyano-6-[(2,4-dichlorobenzyl)amino]-4,5,6,7-tetrahydro-1-benzothien-2-yl}-2-ethylbutanamide

HRID 917348Notes

Reaction equation

HRID 917348 reaction equation
[C:1]([C:3]1[C:7]2[CH2:8][CH2:9][C:10](=O)[CH2:11][C:6]=2[S:5][C:4]=1[NH:13][C:14](=[O:20])[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])#[N:2].[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[CH2:29][NH2:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[C:1]([C:3]1[C:7]2[CH2:8][CH2:9][CH:10]([NH:30][CH2:29][C:23]3[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=3[Cl:21])[CH2:11][C:6]=2[S:5][C:4]=1[NH:13][C:14](=[O:20])[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14852,4-DichlorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58962835N-(3-Cyano-6-oxo-4,5,6,7-tetrahydro-1-benzothien-2-yl)-2-ethylbutanamide

Product 1

HCID 10072447N-{3-Cyano-6-[(2,4-dichlorobenzyl)amino]-4,5,6,7-tetrahydro-1-benzothien-2-yl}-2-ethylbutanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the intermediate isolated in Step C in 100 mL of dichloromethane was added 1.41 mL (12.0 mL) of 1-(2,4-dichlorophenyl)methanamine, followed by 2.54 g (12.0 mmol) of sodium triacetoxyborohydride, and 0.960 mL (16.0 mmol) of acetic acid. After 16 h at ambient temperature, the reaction was quenched with an equal volume of saturated aqueous NaHCO3. The mixture was extracted twice with dichloromethane, and the combined organic layers were dried (Na2SO4), and concentrated in vacuo, affording a yellow solid. Purification by flash chromatography (15% EtOAc in hexane) afforded the title compound as a white solid.

Workup

  1. customthe reaction was quenched with an equal volume of saturated aqueous NaHCO3
  2. extractionThe mixture was extracted twice with dichloromethane
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customaffording a yellow solid
  6. customPurification by flash chromatography (15% EtOAc in hexane)

Sources & evidence

ORD record
ord-ce6dc8cafe144772aae5572fa44ff63e
Source dataset
uspto-grants-2007_09
Patent number
US07273876B2

Reaction notes

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