Diisopropylethylamine → HCID 86623941, 화합물

HRID 1713936노트

반응식

HRID 1713936 반응식
N[C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[NH2:8].[C:15]([O:19][C:20]([NH:22][C:23]1([C:28](O)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:15]([O:19][C:20]([NH:22][C:23]1([C:28]([NH:8][C:7]2[CH:6]=[CH:5][C:4](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])=[CH:3][CH:2]=2)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 27346451-tert-Butoxycarbonylaminocyclopentanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53486922methyl (2E)-3-(3,4-diaminophenyl)prop-2-enoate

생성물 1

HCID 86623941HCID 86623941, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl (2E)-3-(3,4-diaminophenyl)acrylate (from Step 3.1 eq), 1-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (1 eq) in DMF (0.02 M), HATU (1 eq) and DIPEA (3 eq) were added. The reaction mixture was left at RT with stirring overnight. The resulting mixture was partitioned between EtOAc and HCl (1 N). The combined EtOAc layers were washed with brine, and the organic phase was dried over Na2SO4, separated, and evaporated in vacuo to afford methyl (2E)-3-{4-[({1-[(tert-butoxycarbonyl)amino]cyclopentyl}carbonyl)amino]phenyl}acrylate, which was used without further purification. MS (ES+) m/z 404 (M+H)+. The foregoing product was dehydrated by heating it at 65° C. in presence of acetic acid. (0.16 M); the reaction residue was purified by RP-HPLC (Conditions Symmetry (Waters) C18 Column, 7 micron, 19×300 mm; flow: 20 mL/min; Gradient: A H2O+0.1% TFA; B: MeCN+0.1% TFA; 70% A isocratic for 2 min., linear to 20% A in 16 min isocratic for 0.5 min. and linear to 10% A for 2 min). Fractions containing pure product were pooled and lyophilized to give methyl (2E)-3-(2-{1-[(tert-butoxycarbonyl)amino]-cyclopentyl}-1H-benzimidazol-5-yl)acrylate. MS (ES−) m/z 384 (M−H)−.

후처리

  1. waitThe reaction mixture was left at RT
  2. customThe resulting mixture was partitioned between EtOAc and HCl (1 N)
  3. washThe combined EtOAc layers were washed with brine
  4. dry with materialthe organic phase was dried over Na2SO4
  5. customseparated
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-a2caa052cadc4084b52846586b69ba23
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795250B2

반응 노트

불러오는 중…