Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 5-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amide

HRID 1025573ノート

反応式

HRID 1025573 の反応式
C[N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C:35](=[O:39])[N:34]([C:40]1[C:41]([CH2:55][OH:56])=[C:42]([C:46]3[N:50]([CH3:51])[C:49]([C:52](O)=[O:53])=[CH:48][CH:47]=3)[CH:43]=[CH:44][CH:45]=1)[N:33]=[CH:32]2)([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[C:25]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[C:35](=[O:39])[N:34]([C:40]1[C:41]([CH2:55][OH:56])=[C:42]([C:46]3[N:50]([CH3:51])[C:49]([C:52]([NH2:2])=[O:53])=[CH:48][CH:47]=3)[CH:43]=[CH:44][CH:45]=1)[N:33]=[CH:32]2)([CH3:28])([CH3:26])[CH3:27]

参加物

4

反応物 2

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 710086185-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid

生成物 1

HCID 710081215-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amide収率 22.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

HATU (110 mg, 0.288 mmol) was added to a solution of 5-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid (113 mg, 0.262 mmol) in dry THF (15 mL). Ammonia gas was bubbled through the solution. The mixture was stirred at room temperature under NH3 (g) for 16 h. The mixture was concentrated under reduced pressure. The residue was purified by preparative HPLC to give 5-[3-(6-tert-butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amide (25 mg, yield 22%) as a white solid. 1H NMR (300 MHz, CD3OD) δ 8.42 (s, 1H), 8.27 (d, J=8.5 Hz, 1H), 8.02-7.90 (m, 2H), 7.54-7.35 (m, 2H), 7.24-7.13 (m, 2H), 7.02 (d, J=1.9 Hz, 1H), 4.37 (s, 2H), 3.87 (s, 3H), 1.37 (s, 9H). LC-MS calcd for C25H26N4O3 (m/e) 430.20, obsd 883 [2M+Na]+.

後処理

  1. customAmmonia gas was bubbled through the solution
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-52b2534bfaa94ce7b56ba531a4eae980
出典データセット
uspto-grants-2014_05
特許番号
US08729078B2

反応ノート

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