Sodium Carbonate → HCID 68006956, 화합물

HRID 526998노트

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HRID 526998 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C@:11]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])([OH:15])[CH2:10]2)[C:5]([F:21])=[CH:4][N:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]2[C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][N:29](S(C3C=CC(C)=CC=3)(=O)=O)[C:26]2=[N:27][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[ClH:1].[Cl:22][C:23]1[CH:24]=[C:25]2[C:31]([C:2]3[N:7]=[C:6]([NH:8][C@H:9]4[CH2:14][CH2:13][CH2:12][C@:11]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])([OH:15])[CH2:10]4)[C:5]([F:21])=[CH:4][N:3]=3)=[CH:30][NH:29][C:26]2=[N:27][CH:28]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 86667427HCID 86667427, 화합물2회

생성물 1

HCID 68006956HCID 68006956, 화합물

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 679Dimethyl Sulfoxide용매HCID 6342Acetonitrile용매

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온도
130 °C

실험 절차

N-{[(1S,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-hydroxycyclohexyl]-methyl}-acetamide, 46c, (0.2 g, 0.6 mmol) was dissolved in acetonitrile (6 mL) and treated with 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (0.5 g, 1.2 mmol) followed by Pd(PPh3)4 (0.07 g, 0.06 mmol). Aqueous 2M sodium carbonate (3.0 mL, 6.1 mmol) was added, and the vial was sealed and heated in the microwave to 130° C. for 30 min. The organic layer was collected and concentrated in vacuo to provide the crude product, which was dissolved in DMSO and purified by HPLC using 5-70% MeOH/H2O with 6 mM HCl over 15 minutes to provide after concentration 75 mg of N-{[(1S,3S)-3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-hydroxycyclohexyl]methyl}acetamide hydrochloride as an off-white crystalline solid.

후처리

  1. customthe vial was sealed
  2. customThe organic layer was collected
  3. concentrationconcentrated in vacuo
  4. customto provide the crude product, which
  5. custompurified by HPLC
  6. customover 15 minutes

출처 및 근거

ORD 기록
ord-01343cdb79894fec9b1708f42a939e56
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345708B2

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