Water → {(1S,2R)-2-[5-(3-Methyl-1H-indol-7-ylamino)-4-oxo-3,4-dihydro-pyrido[3,4-d]pyridazin-7-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

HRID 629203노트

반응식

HRID 629203 반응식
Cl[C:2]1[N:12]=[C:11]([NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[C:19]3[CH3:23])[C:5]2[C:6](=[O:10])[NH:7][N:8]=[CH:9][C:4]=2[CH:3]=1.CCN(C(C)C)C(C)C.[NH2:33][C@@H:34]1[CH2:39][CH2:38][CH2:37][CH2:36][C@@H:35]1[NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44].O>CN1C(=O)CCC1>[C:43]([O:42][C:41](=[O:47])[NH:40][C@H:35]1[CH2:36][CH2:37][CH2:38][CH2:39][C@H:34]1[NH:33][C:2]1[N:12]=[C:11]([NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[C:19]3[CH3:23])[C:5]2[C:6](=[O:10])[NH:7][N:8]=[CH:9][C:4]=2[CH:3]=1)([CH3:46])([CH3:44])[CH3:45]

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 899724117-Chloro-5-((3-methyl-1H-indol-7-yl)amino)pyrido[3,4-d]pyridazin-4(3H)-one

생성물 1

HCID 89972453{(1S,2R)-2-[5-(3-Methyl-1H-indol-7-ylamino)-4-oxo-3,4-dihydro-pyrido[3,4-d]pyridazin-7-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
120 °C

실험 절차

To 7-chloro-5-(3-methyl-1H-indol-7-ylamino)-3H-pyrido[3,4-d]pyridazin-4-one (177 mg, 0.543 mmol) in NMP (1 ml) in a sealable glass vial, was added DIPEA (0.190 ml, 1.087 mmol) and tert-butyl(1S,2R)-2-aminocyclohexylcarbamate (233 mg, 1.087 mmol). The vial was capped to close and the reaction mixture was heated on a sandbath at 120° C. for 3 days. The resulting mixture was poured into water (20 ml), and extracted with EtOAc (20 ml). The organic phase was washed with water and brine, dried over Na2SO4, then concentrated under vacuum. The residue was triterated with DCM, then collected by filtration and dried to give a gummy solid.

후처리

  1. customThe vial was capped
  2. customto close
  3. extractionextracted with EtOAc (20 ml)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. filtrationcollected by filtration
  8. customdried
  9. customto give a gummy solid

출처 및 근거

ORD 기록
ord-feb174bf91304501956921b59a935653
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315500B2

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