Diisopropylethylamine → HCID 86670471, 화합물

HRID 1911855노트

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HRID 1911855 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:9][CH3:10])[CH:5]=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[C@@H:22]([C@H:23]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:21][CH2:20][C@H:19]1[CH2:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](O)=[O:44])=[CH:41][CH:40]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]([CH3:10])[C:43]([C:42]2[CH:41]=[CH:40][C:39]([CH2:38][C@H:19]3[CH2:20][CH2:21][C@@H:22]([C@H:23]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:18]3[C:16]([O:15][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:17])=[CH:47][CH:46]=2)=[O:44])[CH:5]=[CH:4][CH:3]=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 185259431-(6-Bromopyridin-2-yl)-N-methylmethanamineHCID 67971935HCID 67971935, 화합물

생성물 1

HCID 86670471HCID 86670471, 화합물수율 27.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

1-(6-Bromopyridin-2-yl)-N-methylmethanamine (115 mg, 0.571 mmol) was added to a stirred, room temperature mixture of 4-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)benzoic acid (300 mg, 0.571 mmol), HATU (260 mg, 0.685 mmol, 1.2 equivalents) and DIPEA (498 μL, 2.85 mmol, 5 equivalents) in DMF (2.8 mL). The reaction was stirred at room temperature for 12 hours, and then diluted with EtOAc and partitioned with water. The aqueous layer was extracted with EtOAc (3×), and the combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by normal phase flash chromatography using silica gel (0-50% hexanes/ethyl acetate). The product was collected and concentrated in vacuo to afford the title compound (110 mg, 27%). LC-MS=608.2 & 610.2 (M-Boc+H)+.

후처리

  1. custompartitioned with water
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by normal phase flash chromatography
  8. customThe product was collected
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0d49005e37394ea0b8f9ffafacef9e2b
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604038B2

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