Sodium Carbonate → HCID 68006956、化合物

HRID 526998ノート

反応式

HRID 526998 の反応式
[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

参加物

7

反応物 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、化合物2 回

生成物 1

HCID 68006956HCID 68006956、化合物

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 679Dimethyl Sulfoxide溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-01343cdb79894fec9b1708f42a939e56
出典データセット
uspto-grants-2016_05
特許番号
US09345708B2

反応ノート

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