Acetic Anhydride → N-({6-[(3-fluorophenyl)sulfonyl]-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridin-1-yl}methyl)acetamide

HRID 1616886Notes

Reaction equation

HRID 1616886 reaction equation
COC(OC)CN.C(OC(=O)C)(=O)C.COC(OC)[CH2:18][NH:19][C:20](=[O:22])[CH3:21].[F:25][C:26]1[CH:27]=[C:28]([S:32]([C:35]2[CH:36]=[CH:37][C:38]3[O:42][CH:41]=[C:40]([CH2:43][CH2:44][NH:45][C:46](=O)OC(C)(C)C)[C:39]=3[CH:53]=2)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>ClCCCl.ClCCCl.C(O)(C(F)(F)F)=O>[F:25][C:26]1[CH:27]=[C:28]([S:32]([C:35]2[CH:36]=[CH:37][C:38]3[O:42][C:41]4[CH:46]([CH2:18][NH:19][C:20](=[O:22])[CH3:21])[NH:45][CH2:44][CH2:43][C:40]=4[C:39]=3[CH:53]=2)(=[O:33])=[O:34])[CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 89728Aminoacetaldehyde dimethyl acetalHCID 15289457N-(2,2-Dimethoxyethyl)acetamideHCID 86673691Tert-butyl (2-{5-[(3-fluorophenyl)sulfonyl]-1-benzofuran-3-yl}ethyl)carbamate

Product 1

HCID 67325542N-({6-[(3-fluorophenyl)sulfonyl]-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridin-1-yl}methyl)acetamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 86598524Dce tfaSolvent

Procedure

2,2-Dimethoxyethylamine (16 μL, 1.5 eq) was dissolved in DCE (400 μL), acetic anhydride (15 μL, 1.5 eq) was added and the solution was shaken for 10 min. The resulting solution of N-(2,2-dimethoxyethyl)acetamide in DCE was added to a solution of tert-butyl (2-{5-[(3-fluorophenyl)sulfonyl]-1-benzofuran-3-yl}ethyl)carbamate (800 μL, 0.125 M) in DCE:TFA 1:1. The reaction mixture was shaken at 100° C. for 16 h and the solvent was evaporated. The crude product was purified by preparative LC/MS and concentrated to afford the product as a trifluoroacetic acid salt. MS m/z 403 [M+H]+.

Workup

  1. stirringThe reaction mixture was shaken at 100° C. for 16 h
  2. customthe solvent was evaporated
  3. customThe crude product was purified by preparative LC/MS
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-252c62d9740a41498b62031ecff0cf94
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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