Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 1-oxo-N-[3-(trifluoromethyl)-1,2-oxazol-5-yl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

HRID 1748347노트

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HRID 1748347 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:25]=[C:26]1[C:32]2=[CH:33][C:34]3[CH:35]=[CH:36][C:37]([C:40]([OH:42])=O)=[CH:38][C:39]=3[N:31]2[CH2:30][CH2:29][CH2:28][NH:27]1.C(N=P1N(C)CCCN1C)(C)(C)C.[F:56][C:57]([F:65])([F:64])[C:58]1[CH:62]=[C:61]([NH2:63])[O:60][N:59]=1>ClC(Cl)C>[O:25]=[C:26]1[C:32]2=[CH:33][C:34]3[CH:35]=[CH:36][C:37]([C:40]([NH:63][C:61]4[O:60][N:59]=[C:58]([C:57]([F:65])([F:64])[F:56])[CH:62]=4)=[O:42])=[CH:38][C:39]=3[N:31]2[CH2:30][CH2:29][CH2:28][NH:27]1

참가 물질

6

반응물 4

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 139139963-(Trifluoromethyl)-1,2-oxazol-5-amineHCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2회HCID 178480484HCID 178480484, 화합물

생성물 1

HCID 683233941-oxo-N-[3-(trifluoromethyl)-1,2-oxazol-5-yl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide수율 15.5%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

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온도
60 °C

실험 절차

A mixture of HATU (0.086 g, 0.225 mmol) and 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 0.050 g, 0.205 mmol) in dichlorethane (1 mL) in a microwave vial is heated in a microwave reactor at 60° C. for 60 minutes. Polystyrene bound 2-tert-butylimino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (0.307 g, 0.615 mmol) and 3-trifluoromethyl-isoxazol-5-ylamine (0.094 g, 0.615 mmol) are added to the mixture and the vial is heated in a microwave at 120° C. for an additional 60 minutes. The resin is filtered off and washed several times with DMF. After the removal of solvent, the residue is purified by flash column chromatography using 5% methanol/dichlorormethane to afford title compound (0.012 g, 15.5%) as a white solid.

후처리

  1. additionare added to the mixture
  2. temperaturethe vial is heated in a microwave at 120° C. for an additional 60 minutes
  3. filtrationThe resin is filtered off
  4. washwashed several times with DMF
  5. customAfter the removal of solvent
  6. customthe residue is purified by flash column chromatography

출처 및 근거

ORD 기록
ord-cb794ca266b340dfae756487b04fe00f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150577B2

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