Triethylamine → 2-(dimethylamino)-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethanone

HRID 1505726노트

반응식

HRID 1505726 반응식
[CH2:1]([C:9]1[C:10]([C:22]([F:25])([F:24])[F:23])=[C:11]2[C:15]3=[C:16]([CH2:18][NH:19][CH2:20][CH2:21][N:14]3[CH:13]=[CH:12]2)[CH:17]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[CH3:27][N:28]([CH3:33])[CH2:29][C:30](O)=[O:31].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>C1COCC1>[CH3:27][N:28]([CH3:33])[CH2:29][C:30]([CH:20]1[NH:19][CH2:18][C:16]2=[C:15]3[C:11](=[C:10]([C:22]([F:25])([F:24])[F:23])[C:9]([CH2:1][CH2:2][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:17]2)[CH:12]=[CH:13][N:14]3[CH2:21]1)=[O:31]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866919886-Phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole

생성물 1

HCID 866919962-(dimethylamino)-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethanone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 6-phenethyl-7-(trifluoromethyl)-1,2,3,4-tetrahydro-[1,4]diazepino[6,7,1-hi]indole (prepared as described in Example 2 above, 37 mg, 0.1 mmol) and N,N-dimethylglycine hydrochloride (14 mg, 0.1 mmol) in THF (7 mL) was added triethylamine (50 mg, 0.5 mmol), and 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU; 43 mg, 0.1 mmol). The resulting mixture was stirred overnight, then partitioned between ethyl acetate and water. The organic phase was washed sequentially with NaHCO3 and brine, then dried and concentrated. The residue was purified by reverse-phase chromatography (acetonitrile/water/trifluoroacetic add) to yield 2-(dimethylamino)-1-(6-phenethyl-7-(trifluoromethyl)-3,4-dihydro-[1,4]diazepino[6,7,1-hi]indol-2(1H)-yl)ethanone.

후처리

  1. custompartitioned between ethyl acetate and water
  2. washThe organic phase was washed sequentially with NaHCO3 and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by reverse-phase chromatography (acetonitrile/water/trifluoroacetic add)

출처 및 근거

ORD 기록
ord-3156cc4556094b66b2eaf07f8817a196
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216998B2

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