4-Bromobutyronitrile → N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine

HRID 899593노트

반응식

HRID 899593 반응식
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][NH:18][CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C.Br[CH2:39][CH2:40][CH2:41][C:42]#[N:43]>CC#N>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[CH2:17][N:18]([CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)[CH2:39][CH2:40][CH2:41][CH2:42][NH2:43]

참가 물질

5

반응물 3

HCID 214124-BromobutyronitrileHCID 81531DiisopropylethylamineHCID 219850812-[(5,6,7,8-Tetrahydroquinolin-8-ylamino)-methyl]-benzimidazole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 10126019N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine수율 68.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.169 g, 0.451 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.25 mL, 1.44 mmol) followed by 4-bromobutyronitrile (0.10 mL, 1.01 mmol). The resultant mixture was heated to 80° C. for 5 d then cooled to room temperature. The mixture was concentrated and the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (30:1:1 CH2Cl2—CH3OH—NH4OH) provided 108 mg (54%) of a yellow foam.

후처리

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification of the crude material by column chromatography on silica gel (30:1:1 CH2Cl2—CH3OH—NH4OH)

출처 및 근거

ORD 기록
ord-7c42f56128a04873ba5cfbd9d4699e98
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354932B2

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