Stannous chloride dihydrate → HCID 11292979、化合物

HRID 1294630ノート

反応式

HRID 1294630 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[C:8]([NH:10][S:11]([C:14]2[C:19]3=[N:20][S:21][N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:9]=1)([O-])=O.O.O.Cl[Sn]Cl>CCOC(C)=O.C(Cl)Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:23]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:24])=[C:8]([NH:10][S:11]([C:14]2[C:19]3=[N:20][S:21][N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:9]=1

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 11316813HCID 11316813、化合物

生成物 1

HCID 11292979HCID 11292979、化合物収率 85%

試薬・触媒・溶媒 1

HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

A solution of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-nitro-2-(piperidine-1-carbonyl)-phenyl]-amide (EXAMPLE 2; 90 mg, 2.0 mmol) was dissolved in 1:1 EtOAc/DCM (10 mL), and SnCl2.2H2O (2.3 g, 10 mmol) was added. The mixture was stirred overnight at ambient temperature then concentrated in vacuo. The resulting oil was suspended in DCM and neutralized by shaking with aqueous NaHCO3. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound (69 mg, 1.7 mmol, 82%). TLC (silica gel, 3:1 EtOAc/hexanes): Rf=0.42. MS (ESI): m/z 418 [M+H]+, 440 [M+Na]+. HPLC (reversed-phase): RT=8.15 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.80 (s, 1H), 8.40 (dd, J=8.8 Hz, 1.0 Hz, 1H); 8.15 (dd; J=7.0 Hz, 1.0 Hz, 1H), 7.82 (dd, J=8.8 Hz, 1.0 Hz, 1H), 6.77 (d, J=8.4 Hz, 1H), 6.74 (d, J=2.2 Hz, 1H), 6.19 (dd, J=8.4 Hz, 2.3 Hz, 1H), 5.75 (d, J=2.3 Hz, 2H), 2.96 (bs, 4H), 1.45 (bs, 2H), 1.24 (bs, 4H).

後処理

  1. additionwas added
  2. concentrationthen concentrated in vacuo
  3. stirringneutralized by shaking with aqueous NaHCO3
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7d278cd5a7c049618bda0b4d0611a8a3
出典データセット
uspto-grants-2007_07
特許番号
US07241759B2

反応ノート

読み込み中…