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N-methyl-2-pyrrolidone → HCID 71626821、化合物

HRID 1396342
ノート
印刷プレビュー

反応式

HRID 1396342 の反応式
Cl[C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:10])=[O:9])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][N:13]=2)[CH:3]=1.[C@@H:22]1([NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[NH2:28].CN1CCCC1=O>CO>[NH2:28][C@H:23]1[CH2:24][CH2:25][CH2:26][CH2:27][C@H:22]1[NH:29][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:10])=[O:9])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][N:13]=2)[CH:3]=1
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

5

反応物 3

HCID 13387N-methyl-2-pyrrolidoneHCID 3429171,2-Diaminocyclohexane, cis-HCID 86689712HCID 86689712、化合物

生成物 1

HCID 71626821HCID 71626821、化合物収率 25%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
150 °C

実験手順

A mixture of 6-chloro-4-(5-(methylsulfonyl)pyridin-2-ylamino)pyridazine-3-carboxamide (60 mg, 0.183 mmol), cis-cyclohexane-1,2-diamine (125 mg, 1.1 mmol) and N-methyl-2-pyrrolidinone (2 mL) was heated to 150° C. After 18 h, the reaction mixture was cooled and concentrated in vacuo. Purification by chromatography (spherical silica 20-45 uM, 23 g, Versaflash Supelco, 0 to 5% MeOH containing 10% NH4OH in CH2Cl2, 20 min) gave a solid residue. This residue was dissolved in MeOH and CH2Cl2, then precipitated by addition of cyclohexane. The solid formed was obtained by decantation of the mother liquor, then dried to give 6-(cis-2-aminocyclohexylamino)-4-(5-(methylsulfonyl)pyridin-2-ylamino)pyridazine-3-carboxamide (19 mg, 45.6 μmol, 25%) as a beige solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 12.21 (s, 1H) 8.73 (d, J=2.27 Hz, 1H) 8.48 (br. s., 1H) 8.16 (s, 1H) 8.12 (dd, J=8.69, 2.64 Hz, 1H) 7.75 (br. s., 1H) 7.14 (d, J=8.69 Hz, 1H) 7.03 (d, J=7.93 Hz, 1H) 4.06 (br. s., 1H) 3.26 (s, 3H) 3.09 (br. s., 1H) 1.24-1.78 (m, 10H). LCMS (EI/CI) m/z: 406 [M+H].

後処理

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customPurification by chromatography (spherical silica 20-45 uM, 23 g, Versaflash Supelco, 0 to 5% MeOH containing 10% NH4OH in CH2Cl2, 20 min)
  4. customgave a solid residue
  5. customCH2Cl2, then precipitated by addition of cyclohexane
  6. customThe solid formed
  7. customwas obtained by decantation of the mother liquor
  8. customdried

出典と根拠

ORDレコード
ord-bcf39ef8496b4165a531b734daa5798d
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08901124B2

反応ノート

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