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Lithium diisopropylamide → HCID 178451568, 화합물

HRID 1909064
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HRID 1909064 반응식
[C:1]([Si:5]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[C:17]3[N:19](CN(C)C)[CH:20]=[N:21][C:16]3=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[C:38]([O:42][C:43]([N:45]1[C:49]2=[CH:50][N:51]=[CH:52][C:53]([C:54]3[CH:59]=[C:58]([C:60](OC)=[O:61])[CH:57]=[CH:56][C:55]=3[C:64]#[N:65])=[C:48]2[CH:47]=[CH:46]1)=[O:44])([CH3:41])([CH3:40])[CH3:39].[Li+].CC([N-]C(C)C)C>C1COCC1>[C:38]([O:42][C:43]([N:45]1[C:49]2=[CH:50][N:51]=[CH:52][C:53]([C:54]3[CH:59]=[C:58]([C:60]([C:20]4[NH:19][C:17]5=[N:18][C:13]([N:10]6[CH2:11][CH2:12][CH:7]([O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([C:26]7[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=7)[C:32]7[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=7)[CH2:8][CH2:9]6)=[CH:14][CH:15]=[C:16]5[N:21]=4)=[O:61])[CH:57]=[CH:56][C:55]=3[C:64]#[N:65])=[C:48]2[CH:47]=[CH:46]1)=[O:44])([CH3:41])([CH3:39])[CH3:40]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 2724682Lithium diisopropylamideHCID 66599777HCID 66599777, 화합물HCID 672864874-(2-Cyano-5-methoxycarbonyl-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 178451568HCID 178451568, 화합물수율 90.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of {5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-imidazo[4,5-b]pyridin-3-ylmethyl}-dimethyl-amine (574 mg, 1.12 mmol) and 4-(2-cyano-5-methoxycarbonyl-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (474 mg, 1.26 mmol, 1.1 eq) (Step 1 example 140) in THF (0.1M), cooled to −78° C., was slowly added 1M LDA (2 mol eq). After 1 hr, the reaction mixture was quenched with 50% acetic acid in water (0.25 vols.) at −78° C. The mixture was allowed to warm to room temperature and concentrated to remove most THF. The residue was diluted with EtOAc (20 mL) and basified with aqueous ammonium hydroxide (30%) until pH>8. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was then purified by trituration from Acetonitrile affording 4-(5-{5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-3H-imidazo[4,5-b]pyridine-2-carbonyl}-2-cyano-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester as a red solid (900 mg, 1.01 mmol, 90%). MS ESI m/z 802.7 (M+H)+.

후처리

  1. customthe reaction mixture was quenched with 50% acetic acid in water (0.25 vols.) at −78° C
  2. concentrationconcentrated
  3. customto remove most THF
  4. additionThe residue was diluted with EtOAc (20 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by trituration from Acetonitrile

출처 및 근거

ORD 기록
ord-57fbb9f259114cad8dda66771c4fffdc
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08598217B2

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