Triethylamine → HCID 11547733、化合物

HRID 2264585ノート

反応式

HRID 2264585 の反応式
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]

参加物

9

反応物 4

HCID 8471Triethylamine2 回HCID 94429TriphosgeneHCID 10849964-[(4-Ethylpiperazin-1-yl)methyl]anilineHCID 858916285-(6-Chloro-pyrimidin-4-yloxy)-2,3-dihydro-indole

生成物 1

HCID 11547733HCID 11547733、化合物

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e0d9f1ccb0ff467b8c8c1212df34eb08
出典データセット
uspto-grants-2010_12
特許番号
US07855215B2

反応ノート

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