N,N-Dipropylethylamine → HCID 71280448、化合物

HRID 1497855

反応式

HRID 1497855 の反応式
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:25]=[C:26]1[CH2:29][CH:28]([C:30]([OH:32])=O)[CH2:27]1.N(CC)(CCC)CCC.O[N:43]=[C:44]([C:46]1[CH:47]=[CH:48][C:49]([CH3:64])=[C:50]([NH:52][C:53]([C:55]2[N:59]3[CH:60]=[CH:61][CH:62]=[CH:63][C:58]3=[N:57][CH:56]=2)=[O:54])[CH:51]=1)[NH2:45]>CN(C=O)C>[CH3:64][C:49]1[CH:48]=[CH:47][C:46]([C:44]2[N:43]=[C:30]([CH:28]3[CH2:27][C:26](=[O:25])[CH2:29]3)[O:32][N:45]=2)=[CH:51][C:50]=1[NH:52][C:53]([C:55]1[N:59]2[CH:60]=[CH:61][CH:62]=[CH:63][C:58]2=[N:57][CH:56]=1)=[O:54]

参加物

6

反応物 4

HCID 519799N,N-DipropylethylamineHCID 49133583-Oxocyclobutane-1-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86677441N-(5-(N'-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

生成物 1

HCID 71280448HCID 71280448、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

HATU (1.41 g, 3.72 mmol) was added in one portion to a stirred solution of 3-oxocyclobutanecarboxylic acid (0.405 g, 3.55 mmol) and Pr2NEt (0.62 mL, 3.7 mmol) in dry DMF (5 mL). After 10 minutes, N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (1.0 g, 3.23 mmol) was added in one portion and continued to stir for another 30 minutes. The resulting solution was heated (110° C.) for 30 minutes and then cooled to room temperature. The solvent was evaporated and the residue was partitioned with saturated NH4Cl and EtOAc. The organic layer was dried with MgSO4 and filtered. The residue was purified on silica gel using 10% MeOH in dichloromethane to obtain N-(2-methyl-5-(5-(3-oxocyclobutyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (10). 1H NMR (400 MHz, d6-DMSO) δ 10.20 (s, 1 H), 9.53-9.51 (m, 1 H), 8.71 (s, 1 H), 8.08 (d, J=1.6 Hz, 1 H), 7.91-7.88 (m, 1 H), 7.85 (dd, J=2.0, 8.0 Hz, 1 H), 7.72-7.68 (m, 1 H), 7.51 (d, J=8.4 Hz, 1 H), 7.34-7.30 (m, 1 H), 4.12-4.04 (m, 1 H), 3.70-3.53 (m, 4 H), 2.37 (s, 3 H). MS m/z 388.1 (M+1)+.

後処理

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated
  3. customthe residue was partitioned with saturated NH4Cl and EtOAc
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. customThe residue was purified on silica gel using 10% MeOH in dichloromethane

出典と根拠

ORDレコード
ord-b8a87f3c174741268d93bcd17fc20525
出典データセット
uspto-grants-2015_12
特許番号
US09199981B2

関連ノート

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