Diisopropylethylamine → (R)-Methyl 6-(2-(tert-butoxycarbonylamino)-3-methoxypropylamino)-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate

HRID 711550노트

반응식

HRID 711550 반응식
Cl[C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)[N:3]=1.[NH2:20][CH2:21][C@@H:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:23][O:24][CH3:25].CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:29]([O:28][C:27]([NH:26][C@@H:22]([CH2:23][O:24][CH3:25])[CH2:21][NH:20][C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)[N:3]=1)=[O:33])([CH3:32])([CH3:31])[CH3:30]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 58317582methyl 6-chloro-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinateHCID 59199768tert-butyl N-((2R)-1-amino-3-methoxypropan-2-yl)carbamate

생성물 1

HCID 67238066(R)-Methyl 6-(2-(tert-butoxycarbonylamino)-3-methoxypropylamino)-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
45 °C

실험 절차

To a screw-top vial was added methyl 6-chloro-4-cyano-2-(1-methyl-1H-pyrazol-4-yl)nicotinate (115 mg, 0.416 mmol), (R)-tert-butyl 1-amino-3-methoxypropan-2-ylcarbamate (93 mg, 0.457 mmol), and DIPEA (87 μL, 0.499 mmol) in DMF (308 μL). The resulting yellow solution was stirred for 12 h at 45° C. and then at 50° C. for 6 h. The reaction mixture was diluted with EtOAc (20 mL) and was washed with water (10 mL) and brine (20 mL). The organic layer was collected and dried over Na2SO4 and was concentrated to a yellow oil. The concentrate was purified via standard phase column chromatography eluting with EtOAc and hexanes (50-100% EtOAc gradient) to give the title compound as a light yellow residue (36.5 mg, 20%). [M+H] calc'd for C21H28N6O5, 445. found, 445.

후처리

  1. waitat 50° C. for 6 h
  2. washwas washed with water (10 mL) and brine (20 mL)
  3. customThe organic layer was collected
  4. dry with materialdried over Na2SO4
  5. concentrationwas concentrated to a yellow oil
  6. customThe concentrate was purified via standard phase column chromatography
  7. washeluting with EtOAc and hexanes (50-100% EtOAc gradient)

출처 및 근거

ORD 기록
ord-41c3b0a1b8834706b38a99b096ab0703
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181255B2

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