N-(tert-butoxycarbonyl)glycine → 1,1-dimethylethyl {2-[(2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)amino]-2-oxoethyl}carbamate

HRID 1875028노트

반응식

HRID 1875028 반응식
F[P-](F)(F)(F)(F)F.[N:8]1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[Cl-].N[C:30]1[CH:38]=[C:37]2[C:33]([CH:34]=[C:35]([C:39]([NH:41][CH2:42][C:43]3[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([O:50][C:51]4[CH:56]=[C:55]([C:57]#[N:58])[CH:54]=[C:53]([Cl:59])[CH:52]=4)[C:44]=3[F:60])=[O:40])[NH:36]2)=[CH:32][CH:31]=1.[CH3:61][C:62]([O:65][C:66]([NH:68][CH2:69][C:70]([OH:72])=O)=[O:67])([CH3:64])[CH3:63].C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:49][C:46]1[CH:47]=[CH:48][C:43]([CH2:42][NH:41][C:39]([C:35]2[NH:36][C:37]3[C:33]([CH:34]=2)=[CH:32][C:31]([NH:8][C:70](=[O:72])[CH2:69][NH:68][C:66](=[O:67])[O:65][C:62]([CH3:64])([CH3:63])[CH3:61])=[CH:30][CH:38]=3)=[O:40])=[C:44]([F:60])[C:45]=1[O:50][C:51]1[CH:56]=[C:55]([C:57]#[N:58])[CH:54]=[C:53]([Cl:59])[CH:52]=1

참가 물질

6

반응물 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531DiisopropylethylamineHCID 594513996-Amino-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamideHCID 131720136BOP chloride

생성물 1

HCID 866448881,1-dimethylethyl {2-[(2-{[({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)amino]carbonyl}-1H-indol-5-yl)amino]-2-oxoethyl}carbamate수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

BOP chloride (0.085 g, 0.334 mmol) was added to a solution of 6-amino-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-1H-indole-2-carboxamide (0.065 g, 0.111 mmol), N-{[(1,1-dimethylethyl)oxy]carbonyl}glycine (0.0195 g, 0.111 mmol) and diisopropylethylamine (0.097 mL, 0.557 mmol) in DMF (1 mL). The mixture was stirred at room temperature for 1 hr, then extracted with ethyl acetate and water. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the title compound (0.031 g, 80% pure). ES MS: m/z 624 (M−1).

후처리

  1. extractionextracted with ethyl acetate and water
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-deca4659167e4d0dade99cfbc98c05fc
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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