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Sodium Iodide → Formic acid N-(6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-(4-morpholinylmethyl)-1,3-thiazole-4-carboxamide

HRID 1695774
ノート
印刷プレビュー

反応式

HRID 1695774 の反応式
Cl[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([NH:10][C:11]2[CH:19]=[C:18]([C:20]3[CH:21]=[N:22][C:23]([Cl:31])=[C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:25]=3)[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][N:15]3S(C2C=CC=CC=2)(=O)=O)=[O:9])[N:7]=1.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.CCN(C(C)C)C(C)C.[I-].[Na+].C[Si](C)(C)[O-].[K+]>CC#N.C1COCC1>[CH:8]([OH:9])=[O:44].[Cl:31][C:23]1[N:22]=[CH:21][C:20]([C:18]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[C:11]([NH:10][C:8]([C:6]3[N:7]=[C:3]([CH2:2][N:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)[S:4][CH:5]=3)=[O:9])[CH:19]=2)=[CH:25][C:24]=1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 5238Sodium IodideHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 23668039Potassium trimethylsilanolateHCID 582558462-(Chloromethyl)-N-[6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide

生成物 1

HCID 86653308
Formic acid N-(6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1H-indazol-4-yl)-2-(4-morpholinylmethyl)-1,3-thiazole-4-carboxamide

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

2-(Chloromethyl)-N-[6-{6-chloro-5-[(methylsulfonyl)amino]-3-pyridinyl}-1-(phenylsulfonyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg, 0.078 mmol) was dissolved in MeCN (0.5 ml) and added to morpholine (0.1 mmol). DIPEA (0.026 ml, 0.15 mmol) was added followed by sodium iodide (0.015 g, 0.1 mmol) and the solutions was stirred for 18 hr at 70° C. Potassium trimethylsilanolate (64 mg, 0.5 mmol) was dissolved in THF (0.25 ml) and added to the reaction mixture which was heated to 50° C. for 24 hr. The solution was quenched with aqueous MeCN (50:50, 1 ml) and neutralised. Solvent was removed in a blowdown unit. The crude residue was dissolved in DMF (200 μl), Acetone (200 μl) and water (20 μl) and purified by MDAP (Method D). The solvent was removed in vacuo using the Genevac to give the title compound.

後処理

  1. additionadded to the reaction mixture which
  2. temperaturewas heated to 50° C. for 24 hr
  3. customThe solution was quenched with aqueous MeCN (50:50, 1 ml)
  4. customSolvent was removed in a blowdown unit
  5. dissolutionThe crude residue was dissolved in DMF (200 μl)
  6. customAcetone (200 μl) and water (20 μl) and purified by MDAP (Method D)
  7. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-87a97b2e644045129d9808dab7d8e738
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08163743B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート