Sodium Carbonate → HCID 178481875、化合物

HRID 1915930ノート

反応式

HRID 1915930 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]2[N:23]([CH3:24])[N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[N:29]=[C:30](Br)[S:31][C:32]=2[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:50]2[N:55]=[C:54]([OH:56])[CH:53]=[CH:52][CH:51]=2)O1.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]2[N:23]([CH3:24])[N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[N:29]=[C:30]([C:50]3[CH:51]=[CH:52][CH:53]=[C:54]([OH:56])[N:55]=3)[S:31][C:32]=2[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 86680129tert-butyl N-[4-[[5-[(4S)-4-(benzyloxycarbonylamino)azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]-2-bromo-thiazol-5-yl]carbamateHCID 178431067HCID 178431067、化合物

生成物 1

HCID 178481875HCID 178481875、化合物

試薬・触媒・溶媒 2

HCID 178477754HCID 178477754、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

In a microwave reaction vial, tert-butyl N-[4-[[5-[(4S)-4-(benzyloxycarbonylamino)azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]-2-bromo-thiazol-5-yl]carbamate (200 mg, 0.31 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol (205 mg, 0.93 mmol) and PDCL2(DPPF) (23 mg, 0.031 mmol) were dissolved in acetonitrile (8 mL). Potassium acetate (1.0M, 0.46 mL, 0.46 mmol) was sodium carbonate (1.0M, 0.46 mL, 0.46 mmol) were added and the mixture was irradiated with a microwave for 30 min at 120° C. The mixture was cooled, filtered through Na2SO4 and Celite, concentrated and purified via flash chromatography, methanol/DCM 0% to 10% to afford tert-butyl N-[4-[[5-[(4S)-4-(benzyloxycarbonylamino)azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]-2-(6-hydroxy-2-pyridyl)thiazol-5-yl]carbamate.

後処理

  1. customIn a microwave reaction vial
  2. additionwere added
  3. customthe mixture was irradiated with a microwave for 30 min at 120° C
  4. temperatureThe mixture was cooled
  5. filtrationfiltered through Na2SO4 and Celite
  6. concentrationconcentrated
  7. custompurified via flash chromatography, methanol/DCM 0% to 10%

出典と根拠

ORDレコード
ord-f1a24242ccf143a9a173eaae239072fa
出典データセット
uspto-grants-2013_12
特許番号
US08614206B2

反応ノート

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