1-Methylcyclopropanecarboxylic acid → HCID 44200545、化合物

HRID 2061166ノート

反応式

HRID 2061166 の反応式
[CH3:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:41][N:42]1[C:51]2[C:46](=[CH:47][N:48]=[C:49]([CH3:52])[CH:50]=2)[CH:45]=[C:44]([C:53]2[CH:54]=[C:55]([NH:60]/[C:61](/[NH2:64])=[N:62]/O)[CH:56]=[CH:57][C:58]=2[CH3:59])[C:43]1=[O:65]>CN(C=O)C>[CH3:41][N:42]1[C:51]2[C:46](=[CH:47][N:48]=[C:49]([CH3:52])[CH:50]=2)[CH:45]=[C:44]([C:53]2[CH:54]=[C:55]([NH:60][C:61]3[N:62]=[C:5]([C:2]4([CH3:1])[CH2:4][CH2:3]4)[O:7][N:64]=3)[CH:56]=[CH:57][C:58]=2[CH3:59])[C:43]1=[O:65]

参加物

6

反応物 4

HCID 813261-Methylcyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178422078HCID 178422078、化合物2 回

生成物 1

HCID 44200545HCID 44200545、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 1-methylcyclopropanecarboxylic acid (6 mg, 0.06 mmol) in DMF (1 mL) were added DIPEA (31 μL, 0.18 mmol) and HATU (23 mg, 0.06 mmol). After stirring at rt for 15 min, 17 (20 mg, 0.06 mmol) was added as a solution in DMF (0.5 mL). The reaction was stirred at rt until complete consumption of 17 was determined by LC/MS and then heated at 100° C. for 1 h. Subsequently the reaction was cooled to rt, filtered and purified by preparative LC/MS to give 1,7-dimethyl-3-(2-methyl-5-(5-(1-methylcyclopropyl)-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (A34) as an off white solid. 1H NMR (400 MHz, d6-DMSO) δ 9.87 (s, 1H), 9.13 (s, 1H), 8.05 (s, 1H), 7.87 (s, 1H), 7.37 (dd, J=8, 2 Hz, 1H), 7.30 (d, J=2 Hz, 1H), 7.22 (d, J=8 Hz, 2H), 3.70 (s, 3H), 2.75 (s, 3H), 2.07 (s, 3H), 1.47 (s, 3H), 1.27 (m, 2H), 1.08 (m, 2H). MS m/z 402.4 (M+1).

後処理

  1. temperatureheated at 100° C. for 1 h
  2. temperatureSubsequently the reaction was cooled to rt
  3. filtrationfiltered
  4. custompurified by preparative LC/MS

出典と根拠

ORDレコード
ord-7b56d2ea90594499b62347b6caeef74b
出典データセット
uspto-grants-2012_10
特許番号
US08278452B2

反応ノート

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