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

HRID 917349Notes

Reaction equation

HRID 917349 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].[NH2:21][CH:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:23][OH:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl.C([O-])(O)=O.[Na+]>[C:1]([C:3]1[C:7]2[CH2:8][CH2:9][CH:10]([NH:21][CH:22]([CH2:23][OH:24])[C:25]([CH3:28])([CH3:27])[CH3:26])[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

7

Reactant 4

HCID 176Acetic AcidHCID 41492122-Amino-3,3-dimethylbutan-1-olHCID 5049666Sodium triacetoxyborohydrideHCID 58962835N-(3-Cyano-6-oxo-4,5,6,7-tetrahydro-1-benzothien-2-yl)-2-ethylbutanamide

Product 1

HCID 58962825N-(3-Cyano-6-{[1-(hydroxymethyl)-2,2-dimethylpropyl]amino}-4,5,6,7-tetrahydro-1-benzothien-2-yl)-2-ethylbutanamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of the intermediate isolated in Example 9, Step C, in 40 mL of dichloromethane was added 0.452 g (3.90 mmol) of 2-amino-3,3-dimethylbutan-1-ol, followed by 1.24 g (5.9 mmol) of sodium triacetoxyborohydride and 0.468 mL (7.80 mmol) of acetic acid. After 16 h at ambient temperature the reaction was diluted with an equal volume of saturated aqueous NaHCO3. The organic layer was dried (Na2SO4) and concentrated in vacuo. Purification by preparative reversed phase HPLC afforded the title compound (TFA salt).

Workup

  1. dry with materialThe organic layer was dried (Na2SO4)
  2. concentrationconcentrated in vacuo
  3. customPurification by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-caf7821ad0d54ab6abf035ce69687821
Source dataset
uspto-grants-2007_09
Patent number
US07273876B2

Reaction notes

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