Triethylamine → tert-butyl (2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl)carbamate

HRID 1505729노트

반응식

HRID 1505729 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH2:32]([C:40]1[C:41]([C:53]([F:56])([F:55])[F:54])=[C:42]2[C:46]3=[C:47]([CH2:49][NH:50][CH2:51][CH2:52][N:45]3[CH:44]=[CH:43]2)[CH:48]=1)[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl.[C:58]([NH:65][CH2:66][C:67](O)=[O:68])([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59]>C1COCC1>[O:68]=[C:67]([CH:51]1[NH:50][CH2:49][C:47]2=[C:46]3[C:42](=[C:41]([C:53]([F:56])([F:55])[F:54])[C:40]([CH2:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[CH:48]2)[CH:43]=[CH:44][N:45]3[CH2:52]1)[CH2:66][NH:65][C:58](=[O:59])[O:60][C:61]([CH3:63])([CH3:62])[CH3:64]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19004789N-Boc-glycine hydrochlorideHCID 866919886-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole

생성물 1

HCID 86692000tert-butyl (2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl)carbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

HATU (172 mg, 0.45 mmol) and triethylamine (1.97 mmol) was added to a mixture of 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (prepared as described in Example 2 above, 150 mg, 0.39 mmol) and N-Boc-glycine hydrochloride (72 mg, 0.41 mmol) in THF (7 mL). After stirring overnight, the resulting mixture was partitioned between ethyl acetate and water. The organic phase was washed sequentially with NaHCO3 (sat'd., aq) and brine, then dried and concentrated. The resulting residue was purified by reverse-phase chromatography to yield tert-butyl (2-oxo-2-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethyl)carbamate (200 mg, MS m/z 502 (MH+).

후처리

  1. customthe resulting mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed sequentially with NaHCO3 (sat'd., aq) and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting residue was purified by reverse-phase chromatography

출처 및 근거

ORD 기록
ord-ed4aaa68e64445aa8bf118ba40d17a5a
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216998B2

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