Acetic Acid → HCID 59424239, compound

HRID 1172873Notes

Reaction equation

HRID 1172873 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:10][C:6]=2[CH:5]=1)(=O)[CH3:2].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH:25][CH:1]([C:4]2[CH:17]=[CH:16][C:7]3[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:10][C:6]=3[CH:5]=2)[CH3:2])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57443972HCID 57443972, compound

Product 1

HCID 59424239HCID 59424239, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Ethyl 6-acetyl-1-benzothiophene-2-carboxylate (0.3 g, 1.21 mmol) was dissolved in DCE (3.0 mL). 4-methoxybenzyl amine was then added to the reaction followed by acetic acid (0.1 mL, 1.69 mmol) and NaBH(OAc)3 (0.41 g, 1.93 mmol). The reaction was allowed to stir for 5 d at room temperature before it was quenched with saturated sodium bicarbonate solution. The reaction mixture was then extracted with ethyl acetate (3×) and the combined organic layers was dried over Na2SO4. After concentrating in vacuo, the crude reaction mixture was purified by flash column chromatography to provide the amine. 1H (600 MHz, CDCl3) δ 8.03 (s, 1H), 7.84 (s, 1H), 7.82 (s, 1H), 7.41 (d, J=8.9 Hz, 1H), 7.18 (d, J=8.5 Hz, 2H), 6.85 (d, J=8.5 Hz, 2H), 4.40 (q, J=7.1 Hz, 2H), 3.93 (q, J=6.5 Hz, 1H), 3.79 (s, 3H), 3.57 (dd, J=21.0, 12.9 Hz, 2H), 1.42-1.26 (m, 6H). MS: cal'd (MH+) 370, exp (MH+): 370.

Workup

  1. customwas quenched with saturated sodium bicarbonate solution
  2. extractionThe reaction mixture was then extracted with ethyl acetate (3×)
  3. dry with materialthe combined organic layers was dried over Na2SO4
  4. concentrationAfter concentrating in vacuo
  5. customthe crude reaction mixture
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-fd2eaa16984948eeb68524c8a792d434
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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