Dimethylacetamide → HCID 24946166、化合物

HRID 1803532ノート

反応式

HRID 1803532 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[C:5]2[Cl:13].Cl.[O:15]1[C:20]2[CH:21]=[CH:22][CH:23]=[C:24](NC)[C:19]=2[O:18][CH2:17][CH2:16]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].C[C:80]([N:82](C)C)=O>CCOC(C)=O>[Cl:13][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:82][CH2:80][C:24]3[C:19]4[O:18][CH2:17][CH2:16][O:15][C:20]=4[CH:21]=[CH:22][CH:23]=3)[CH:3]=2)[C:8](=[O:12])[NH:7][N:6]=1

参加物

7

反応物 5

HCID 31374DimethylacetamideHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 533084876-Bromo-4-chlorophthalazin-1(2H)-oneHCID 67417056HCID 67417056、化合物

生成物 1

HCID 24946166HCID 24946166、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture 6-bromo-4-chloro-2H-phthalazin-1-one (150 mg, 0.58 mmol), (2,3-dihydro-benzo[1,4]dioxin-5-yl)-methylamine hydrochloride (129 mg, 0.64 mmol), Pd-2(dba)3 (53 mg, 0.058 mmol), rac-BINAP (132 mg, 0.17 mmol) and NaOt-Bu (200 mg, 2.1 mmol) in DMA (6 mL) was heated at 80° C. for 1 h. The mixture was allowed to cool, diluted with EtOAc (25 mL) and washed with water (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated. Chromatography on silica (EtOAc/hexanes) yielded the title compound. 4-Chloro-6-[(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-amino]-2H-phthalazin-1-one: 41 mg (20.6%): m/z (M+H)=344. 1H-NMR (DMSO-d6) δ: 12.33 (s, 1H), 7.92 (d, 1H), 7.53 (m, 1H), 7.13 (dd, 1H), 6.82 (m, 4H), 4.33 (m, 4H), 4.26 (m, 2H).

後処理

  1. temperatureto cool
  2. washwashed with water (25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-e09a738d1a014e329579d024d4f300ed
出典データセット
uspto-grants-2013_01
特許番号
US08349836B2

反応ノート

読み込み中…