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Triethylamine → Tert-butyl 4-[({[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)amino]butanoate

HRID 1715301
ノート
印刷プレビュー

反応式

HRID 1715301 の反応式
[C:1]([NH:4][C:5]1[S:6][C:7]([C:11]2[N:12]=[C:13]([C:16](NCC3CCCO3)=O)[S:14][CH:15]=2)=[C:8]([CH3:10])[N:9]=1)(=[O:3])C.Cl.[NH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].[CH2:37]([N:39](CC)CC)C>CN(C=O)C>[C:37]([CH2:16][C:13]1[S:14][CH:15]=[C:11]([C:7]2[S:6][C:5]([NH:4][C:1]([NH:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:3])=[N:9][C:8]=2[CH3:10])[N:12]=1)#[N:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 119895252'-(Acetylamino)-4'-methyl-N-(tetrahydrofuran-2-ylmethyl)-4,5'-bi-1,3-thiazole-2-carboxamide2 回HCID 24750478Tert-butyl 4-aminobutanoate hydrochloride

生成物 1

HCID 11988517Tert-butyl 4-[({[2-(cyanomethyl)-4'-methyl-4,5'-bi-1,3-thiazol-2'-yl]amino}carbonyl)amino]butanoate

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

N-[2-(cyanomethyl)-4′-methyl-4,5′-bi-1,3-thiazol-2′-yl]-1H-imidazole-1-carboxamide (Intermediate 6) (160 mg; 0.48 mmol; 1 eq) is dissolved in DMF (8 ml). Tert-butyl 4-aminobutanoate hydrochloride (94.8 mg; 0.48 mmol; 1 eq) and triethylamine (148 μl; 1.07 mmol; 2.20 eq) are added. After less than 1 min, the mixture becomes homogeneous. After 30 min the reaction is complete. DMF is removed under reduced pressure. The resulting crude oil is dissolved in DCM and washed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution. The organic layer is dried over Na2SO4, filtered and concentrated. The resulting crude product is purified by preparative HPLC. The purified fractions are neutralized with NaHCO3 sat. solution and the desired compound is extracted with DCM.

後処理

  1. waitAfter less than 1 min
  2. customDMF is removed under reduced pressure
  3. dissolutionThe resulting crude oil is dissolved in DCM
  4. washwashed twice with NH4Cl sat. solution and twice with NaHCO3 sat. solution
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting crude product is purified by preparative HPLC
  9. extractionthe desired compound is extracted with DCM

出典と根拠

ORDレコード
ord-fc98975c7d1d488ca22fb17f625dc189
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07799814B2

反応ノート

読み込み中…

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