Diisopropylethylamine → (5-{[(3-Benzyl-[1,2,4]oxadiazole-5-carbonyl)-amino]-methyl}-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester

HRID 928364노트

반응식

HRID 928364 반응식
[CH2:1]([C:8]1[N:12]=[C:11]([C:13]([OH:15])=O)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([O:20][C:21](=[O:33])[NH:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([CH2:30][NH2:31])=[C:25]([CH3:32])[N:24]=1)([CH3:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:16]([O:20][C:21](=[O:33])[NH:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([CH2:30][NH:31][C:13]([C:11]2[O:10][N:9]=[C:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:12]=2)=[O:15])=[C:25]([CH3:32])[N:24]=1)([CH3:19])([CH3:18])[CH3:17]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22475372N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamideHCID 498745143-Benzyl-1,2,4-oxadiazole-5-carboxylic acid

생성물 1

HCID 58081166(5-{[(3-Benzyl-[1,2,4]oxadiazole-5-carbonyl)-amino]-methyl}-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-Benzyl-[1,2,4]oxadiazole-5-carboxylic acid (330 mg, 1.5 mmol), (5-Aminomethyl-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (389 mg, 1.5 mmol), HATU (1.1 g, 3.1 mmol) and DIPEA (0.8 mL, 4.7 mmol) in 10 mL DMF was stirred at room temperature for 16 h. The mixture was evaporated and the residue was partitioned between ethyl acetate and 1 N aq. HCl. The organic layer was dried over MgSO4 and evaporated in vacuo. The crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min). LCMS (method A) RtA=1.834 min; [M+H]+=438.1.

후처리

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between ethyl acetate and 1 N aq. HCl
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min)
  6. customLCMS (method A) RtA=1.834 min

출처 및 근거

ORD 기록
ord-dfb517471d14478ea2900f9e53dcee56
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290485B2

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