1,1'-Carbonyldiimidazole → tert-butyl [(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]carbamate

HRID 2108836노트

반응식

HRID 2108836 반응식
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.[H][H].C1N=CN([C:28](N2C=NC=C2)=[O:29])C=1>C1COCC1.[Pd]>[CH3:1][N:2]1[C:3]2[CH:4]=[C:5]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=[CH:7][C:8]=2[NH:9][C:28]1=[O:29]

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 86609347HCID 86609347, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 86609348tert-butyl [(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]carbamate수율 77.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of tert-butyl [(3-methylamino-4-nitrophenyl)methyl]carbamate (864 mg, 3.07 mmol) and 10% Pd—C (100 mg) in THF was charged with hydrogen carefully. After stirring for 6 hours at room temperature, the reaction was recharged with nitrogen. Then, filtration, evaporation gave the residue, which was used for further reaction without purification. To the THF solution of the above, CDI (597 mg, 3.68 mmol) was added and the mixture was stirred for 4 hours at room temperature. After evaporation, purification through silica gel column chromatography eluting with CH2Cl2/MeOH (15:1) gave tert-butyl [(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]carbamate as white solid (658 mg, 77%). 1H NMR (CDCl3): δ 1.47 (9H, s), 4.35 (2H, d, J=5.2 Hz), 4.92 (2H, brs), 6.86-7.10 (3H, m), 9.73 (1H, brs) MS (ESI) m/z 278 (M+H)+.

후처리

  1. filtrationThen, filtration, evaporation
  2. customgave the residue, which
  3. customwas used for further reaction without purification
  4. stirringthe mixture was stirred for 4 hours at room temperature
  5. customAfter evaporation, purification through silica gel column chromatography
  6. washeluting with CH2Cl2/MeOH (15:1)

출처 및 근거

ORD 기록
ord-510fa389d8134ca0941a71e82adbc96e
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514457B2

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