Diisopropylethylamine → (3R,9aS)-tert-butyl 8-(3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carbonyl)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

HRID 2175932노트

반응식

HRID 2175932 반응식
[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C@@H:10]2[CH2:15][N:14]3[CH2:16][CH2:17][NH:18][CH2:19][C@H:13]3[CH2:12][N:11]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[N:28]1([C:33]2[N:38]=[CH:37][C:36]3[CH:39]([C:42](O)=[O:43])[CH2:40][CH2:41][C:35]=3[CH:34]=2)[CH:32]=[N:31][N:30]=[N:29]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[N:28]1([C:33]2[N:38]=[CH:37][C:36]3[CH:39]([C:42]([N:18]4[CH2:17][CH2:16][N:14]5[CH2:15][C@@H:10]([C:5]6[CH:6]=[CH:7][C:8]([F:9])=[C:3]([C:1]#[N:2])[C:4]=6[CH3:27])[N:11]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:12][C@@H:13]5[CH2:19]4)=[O:43])[CH2:40][CH2:41][C:35]=3[CH:34]=2)[CH:32]=[N:31][N:30]=[N:29]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 675172303-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylic acidHCID 86727053(3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

생성물 1

HCID 86727115(3R,9aS)-tert-butyl 8-(3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carbonyl)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (3R,9aS)-tert-butyl 3-(3-cyano-4-fluoro-2-methylphenyl)hexahydro-1H-pyrazino[1,2-a]pyrazine-2(6H)-carboxylate [I-18A](250 mg, 0.668 mmol) and 3-(1H-tetrazol-1-yl)-6,7-dihydro-5H-cyclopenta[c]pyridine-7-carboxylic acid [I-65] (201 mg, 0.868 mmol) in DMF (4 mL) was added HATU (381 mg, 1.00 mmol) followed by addition of diisopropylethylamine (350 μL, 2.00 mmol). The resulting solution was stirred at rt for 1 h. Ethyl acetate (100 mL) was added and the mixture was washed with saturated sodium bicarbonate (3×100 mL), dried over sodium sulphate, concentrated and the residue was purified by preparative TLC eluting with 10% methanol/methylene chloride to give the title compound. LC/MS: (M+1)+: 588.2.

후처리

  1. washthe mixture was washed with saturated sodium bicarbonate (3×100 mL)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated
  4. customthe residue was purified by preparative TLC
  5. washeluting with 10% methanol/methylene chloride

출처 및 근거

ORD 기록
ord-d0d1b80575d64b069446964f3dda6fbe
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062070B2

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