Diisopropylethylamine → Tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate

HRID 1946680

반응식

HRID 1946680 반응식
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.ClC1N=CN=C(C(NC2C=CC(O)=CC=2)=O)C=1.[C:28]([O:32][C:33](=[O:43])[NH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1)([CH3:31])([CH3:30])[CH3:29].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:42][C:39]2[CH:40]=[CH:41][C:36]([CH2:35][NH:34][C:33](=[O:43])[O:32][C:28]([CH3:30])([CH3:31])[CH3:29])=[CH:37][CH:38]=2)=[O:9])[CH:3]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2756041tert-butyl N-[(4-aminophenyl)methyl]carbamateHCID 184220986-Chloropyrimidine-4-carbonyl chlorideHCID 594468766-chloro-N-(4-hydroxyphenyl)pyrimidine-4-carboxamide

생성물 1

HCID 59447092Tert-butyl (4-{[(6-chloropyrimidin-4-yl)carbonyl]amino}benzyl)carbamate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a cooled (0° C.) solution of 6-chloropyrimidine-4-carbonyl chloride in DCM (30 mL), obtained as described above for Intermediate 7, step 1 (1.43 g; 8.10 mmol) was added dropwise, during a period of 15 minutes, a solution of (4-amino-benzyl)-carbamic acid tert-butyl ester (Astatech, 1.50 g; 6.75 mmol) and DIEA (2.33 ml; 13.5 mmol) in DCM (5 mL). At the end of addition the reaction mixture was concentrated in vacuo, diluted with water and extracted with EtOAc. The resulting precipitate was filtered and dried under vacuum. The mother liquors were dried on MgSO4, concentrated under vacuum to give a residue, which was precipitated from cyclohexane. The two solids were combined to give the title compound as a brown solid.

후처리

  1. customobtained
  2. additionwas added dropwise, during a period of 15 minutes
  3. additionAt the end of addition the reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additiondiluted with water
  6. extractionextracted with EtOAc
  7. filtrationThe resulting precipitate was filtered
  8. customdried under vacuum
  9. customThe mother liquors were dried on MgSO4
  10. concentrationconcentrated under vacuum
  11. customto give a residue, which
  12. customwas precipitated from cyclohexane

출처 및 근거

ORD 기록
ord-88b2f155075c41a8b77e561f108d2152
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399448B2

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