Triethylamine → HCID 11547733, 화합물

HRID 2264585노트

반응식

HRID 2264585 반응식
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH2:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)[CH3:14].CCN(CC)CC.[Cl:36][C:37]1[N:42]=[CH:41][N:40]=[C:39]([O:43][C:44]2[CH:45]=[C:46]3[C:50](=[CH:51][CH:52]=2)[NH:49][CH2:48][CH2:47]3)[CH:38]=1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].O.CCOC(C)=O>[CH2:13]([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([NH:26][C:2]([N:49]3[C:50]4[C:46](=[CH:45][C:44]([O:43][C:39]5[CH:38]=[C:37]([Cl:36])[N:42]=[CH:41][N:40]=5)=[CH:52][CH:51]=4)[CH2:47][CH2:48]3)=[O:4])=[CH:27][CH:28]=2)[CH2:17][CH2:16]1)[CH3:14]

참가 물질

9

반응물 4

HCID 8471Triethylamine2회HCID 94429TriphosgeneHCID 10849964-[(4-Ethylpiperazin-1-yl)methyl]anilineHCID 858916285-(6-Chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole

생성물 1

HCID 11547733HCID 11547733, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 6344Dichloromethane용매3회HCID 8857Ethyl Acetate용매HCID 10340Sodium Carbonate용매

실험 절차

104 mg (0.35 mMol) triphosgene are dissolved in 13 ml ice-cooled CH2Cl2. Then a solution of 230 mg (1.05 mMol) 4-(4-ethylpiperazin-1-ylmethyl)-aniline and 209 μl (1.50 mMol) Et3N in 6 ml CH2Cl2 is added during 8 min. After 3 additional minutes, the mixture is warmed up to rt by a water bath and then a solution of 1.0 mMol 5-(6-chloro-pyrimidin-4-yloxy)-2,3-dihydro-1H-indole (Step 14.1) and 139 μl (1.00 mMol) Et3N in 6 ml CH2Cl2 is added during 8 min. After 2 h at rt, the mixture is diluted with sat. Na2CO3 solution/water 1:1 and EtOAc, the aqueous phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Crystallization from DIPE gives the title compound: MS: [M+1]+=493/495; TLC(CH2Cl2/MeOH/NH3conc. 90:10:1): Rf=0.24; HPLC: AtRet=10.5.

후처리

  1. customthe aqueous phase separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic layers are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customCrystallization from DIPE

출처 및 근거

ORD 기록
ord-e0d9f1ccb0ff467b8c8c1212df34eb08
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07855215B2

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