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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
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HRID 1715301 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 119895252'-(Acetylamino)-4'-methyl-N-(tetrahydrofuran-2-ylmethyl)-4,5'-bi-1,3-thiazole-2-carboxamide2회HCID 24750478Tert-butyl 4-aminobutanoate hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fc98975c7d1d488ca22fb17f625dc189
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07799814B2

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