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Water → HCID 178457295、化合物

HRID 386691
ノート
印刷プレビュー

反応式

HRID 386691 の反応式
[Cl:1][C:2]1[CH:12]=[C:11]([CH2:13][CH2:14][C:15]([N:17]2[CH2:38][CH2:37][C:20]3([NH:24]/[C:23](=[N:25]/[C:26]([C:28]4[C:33]([NH2:34])=[N:32][C:31]([NH2:35])=[C:30]([Cl:36])[N:29]=4)=[O:27])/[NH:22][CH2:21]3)[CH2:19][CH2:18]2)=[O:16])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].Cl[CH2:40][C:41]([N:43]([CH2:47][CH2:48][CH3:49])[CH2:44][CH2:45][CH3:46])=[O:42].C(=O)([O-])O.[Na+].O>CN(C=O)C>[CH2:44]([N:43]([CH2:47][CH2:48][CH3:49])[C:41]([CH2:40][O:7][C:6](=[O:8])[CH2:5][O:4][C:3]1[CH:9]=[CH:10][C:11]([CH2:13][CH2:14][C:15]([N:17]2[CH2:18][CH2:19][C:20]3([NH:24]/[C:23](=[N:25]/[C:26]([C:28]4[C:33]([NH2:34])=[N:32][C:31]([NH2:35])=[C:30]([Cl:36])[N:29]=4)=[O:27])/[NH:22][CH2:21]3)[CH2:37][CH2:38]2)=[O:16])=[CH:12][C:2]=1[Cl:1])=[O:42])[CH2:45][CH3:46]
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

6

反応物 4

HCID 962WaterHCID 2196472-chloro-N,N-dipropylacetamideHCID 516892Sodium BicarbonateHCID 178508778HCID 178508778、化合物

生成物 1

HCID 178457295HCID 178457295、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution of [2-Chloro-4-(3-{2-[(E)-3,5-diamino-6-chloro-pyrazine-2-carbonylimino]-1,3,8-triaza-spiro[4.5]dec-8-yl}-3-oxo-propyl)-phenoxy]-acetic acid (step 2) (4.82 g, 8.52 mmol) in DMF (70 ml) was treated with 2-chloro-N,N-dipropyl-acetamide (3.18 g, 17.9 mmol) followed by sodium hydrogen carbonate (2.26 g, 26.9 mmol) and the resulting suspension heated to 60° C. overnight. Water (500 ml) was added to the reaction mixture and the product extracted with EtOAc (1000 ml). The organic extracts were washed with water (500 ml) and brine (500 ml), dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with 0-12% 2N ammonia in ethanol in DCM followed by further purification by C18 reverse phase chromatography eluting with MeCN/water afforded the title product; 1H NMR (400 MHz, DMSO-d6) δ 8.43 (1H, br s), 8.36 (1H, br s), 7.34 (1H, d), 7.14 (1H, dd), 7.02 (1H, s), 6.71 (2H, br s), 4.95 (2H, s), 4.89 (2H, s), 3.67-3.53 (2H, m), 3.39 (3H, br s), 3.19 (2H, t), 3.13 (2H, t), 2.75 (2H, t), 2.62 (2H, t), 1.65-1.41 (8H, m), 0.85 (3H, t), 0.80 (3H, t). LC-MS Rt 4.11 mins; 706.5 [M+H]+, Method 10minLC_v003.

後処理

  1. extractionthe product extracted with EtOAc (1000 ml)
  2. washThe organic extracts were washed with water (500 ml) and brine (500 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica eluting with 0-12% 2N ammonia in ethanol in DCM
  6. customfollowed by further purification by C18 reverse phase chromatography
  7. washeluting with MeCN/water

出典と根拠

ORDレコード
ord-1b9ead5ac0b744098026c059bb6f6a74
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08372845B2

反応ノート

読み込み中…

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