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 1025573노트

반응식

HRID 1025573 반응식
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]

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-52b2534bfaa94ce7b56ba531a4eae980
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729078B2

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