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4-Methylphenyl isocyanate → (2S)-2-(tert-butoxy)-2-(7-(8-fluoro-5-methylchroman-6-yl)-5-methyl-2-(3-(p-tolyl)ureido)pyrazolo[1,5-a]pyrimidin-6-yl)acetic acid

HRID 1468752
ノート
印刷プレビュー

反応式

HRID 1468752 の反応式
[NH2:1][C:2]1[CH:32]=[C:5]2[N:6]=[C:7]([CH3:31])[C:8]([C@H:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([OH:25])=[O:24])=[C:9]([C:10]3[C:11]([CH3:21])=[C:12]4[C:17](=[C:18]([F:20])[CH:19]=3)[O:16][CH2:15][CH2:14][CH2:13]4)[N:4]2[N:3]=1.[N:33]([C:36]1[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=1)=[C:34]=[O:35].CCN(C(C)C)C(C)C>C1COCC1>[C:27]([O:26][C@@H:22]([C:8]1[C:7]([CH3:31])=[N:6][C:5]2[N:4]([N:3]=[C:2]([NH:1][C:34]([NH:33][C:36]3[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=3)=[O:35])[CH:32]=2)[C:9]=1[C:10]1[C:11]([CH3:21])=[C:12]2[C:17](=[C:18]([F:20])[CH:19]=1)[O:16][CH2:15][CH2:14][CH2:13]2)[C:23]([OH:25])=[O:24])([CH3:28])([CH3:29])[CH3:30]
参加物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 693254-Methylphenyl isocyanateHCID 81531DiisopropylethylamineHCID 71730302(2S)-2-(2-amino-7-(8-fluoro-5-methylchroman-6-yl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetic acid

生成物 1

HCID 71730820(2S)-2-(tert-butoxy)-2-(7-(8-fluoro-5-methylchroman-6-yl)-5-methyl-2-(3-(p-tolyl)ureido)pyrazolo[1,5-a]pyrimidin-6-yl)acetic acid

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

A mixture of Example 1 (22 mg, 0.050 mmol), 1-isocyanato-4-methylbenzene (7.28 mg, 0.055 mmol), Hunig's base (0.026 mL, 0.149 mmol) in THF (2 mL) was stirred at rt for 16 h. It was then concentrated and purified by prep HPLC (TFA/MeOH). The fractions were combined and adjusted pH=6 using 1N NaOH. The residue was adjusted pH=3-4 by adding 1-2 drops of 1N HCl. It was then extracted with EtOAc, dried, filtered and concentrated to obtained Example (18 mg, 60%) as light yellow solid. LCMS (M+H)=576.31.

後処理

  1. concentrationIt was then concentrated
  2. custompurified by prep HPLC (TFA/MeOH)
  3. additionby adding 1-2 drops of 1N HCl
  4. extractionIt was then extracted with EtOAc
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtained Example (18 mg, 60%) as light yellow solid

出典と根拠

ORDレコード
ord-33de800432b7427c933889252bd688ba
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09006235B2

反応ノート

読み込み中…

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