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

HRID 1616886노트

반응식

HRID 1616886 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매2회HCID 86598524Dce tfa용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-252c62d9740a41498b62031ecff0cf94
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765779B2

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