Sodium Carbonate → N,N-dimethyl-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzenesulfonamide

HRID 500184

反応式

HRID 500184 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][N:8]([CH3:27])[S:9]([C:12]1[CH:17]=[CH:16][C:15](B2OC(C)(C)C(C)(C)O2)=[CH:14][CH:13]=1)(=[O:11])=[O:10].Br[C:29]1[CH:30]=[N:31][C:32]([NH2:35])=[N:33][CH:34]=1.Cl[CH:37]([C:40]1([C:43]2[CH:44]=[C:45]3[C:50](=[CH:51][CH:52]=2)[N:49]=[CH:48][CH:47]=[CH:46]3)[CH2:42][CH2:41]1)[CH:38]=O>O.C(O)C.C1(C)C=CC=CC=1.C(O)(C)C.CO.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>[CH3:27][N:8]([CH3:7])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([C:29]2[CH:30]=[N:31][C:32]3[N:33]([C:37]([C:40]4([C:43]5[CH:44]=[C:45]6[C:50](=[CH:51][CH:52]=5)[N:49]=[CH:48][CH:47]=[CH:46]6)[CH2:42][CH2:41]4)=[CH:38][N:35]=3)[CH:34]=2)=[CH:16][CH:17]=1)(=[O:10])=[O:11]

参加物

11

反応物 4

HCID 10340Sodium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 3868489N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamideHCID 86621504Chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde

生成物 1

HCID 25144949N,N-dimethyl-4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzenesulfonamide

試薬・触媒・溶媒 6

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 3776Isopropanol溶媒

反応条件

温度
120 °C

実験手順

Sodium carbonate (79.5 mg) in water (0.5 mL) was added to a mixture of N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (93.4 mg, 0.3 mmol), 5-bromopyrimidin-2-amine (43.5 mg, 0.25 mmol) and tetrakis(triphenylphosphine)palladium (8.7 mg, 0.0075 mmol) in ethanol (1.0 mL) and toluene (1.0 mL). The resulting mixture was heated at 120° C. for 2 h. The mixture was diluted with water, filtered, and washed with water. The solid was collected and dried. Chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde (45.0 mg, 0.183 mmol) in isopropanol (1.0 mL) was added to the above solid. The mixture was heated at 90° C. overnight. After cooling to RT, the mixture was diluted with methanol, and purified by RP-HPLC (pH 10) to give the desired product. LCMS: (M+H)=470.1.

後処理

  1. filtrationfiltered
  2. washwashed with water
  3. customThe solid was collected
  4. customdried
  5. temperatureThe mixture was heated at 90° C. overnight
  6. temperatureAfter cooling to RT
  7. custompurified by RP-HPLC (pH 10)

出典と根拠

ORDレコード
ord-0e0ee58eeef5419aa23b3a0ff5b6b767
出典データセット
uspto-grants-2010_08
特許番号
US07767675B2

関連ノート

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