Triethylamine → HCID 22291629、化合物

HRID 968112ノート

反応式

HRID 968112 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([Cl:11])=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[NH2:43][C:44]1[CH:66]=[CH:65][C:47]2[CH2:48][CH2:49][C:50]3[C:51]([C:62]([NH2:64])=[O:63])=[N:52][N:53]([C:55]4[CH:60]=[CH:59][C:58]([F:61])=[CH:57][CH:56]=4)[C:54]=3[C:46]=2[CH:45]=1.CC1C(C(O)=O)=CN=C(Cl)C=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([Cl:11])=[CH:9][N:10]=1)[C:5]([NH:43][C:44]1[CH:66]=[CH:65][C:47]2[CH2:48][CH2:49][C:50]3[C:51]([C:62]([NH2:64])=[O:63])=[N:52][N:53]([C:55]4[CH:56]=[CH:57][C:58]([F:61])=[CH:59][CH:60]=4)[C:54]=3[C:46]=2[CH:45]=1)=[O:7]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 27360872,5-dichloropyridine-4-carboxylic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222917476-Chloro-4-methylpyridine-3-carboxylic acidHCID 22291910HCID 22291910、化合物

生成物 1

HCID 22291629HCID 22291629、化合物収率 73.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2,5-Dichloroisonicotinic acid (1.65 g, 0.0086 mol), HATU (3.27 g, 0.0086 mol), and Et3N (2.32 mL, 0.0166 mol) were added to a solution of the title compound of Example 244 (1.85 g, 0.00574 mol) in 29 mL of DMF. The reaction mixture was stirred at room temperature for 3 h. The completion of the reaction was confirmed by monitoring the disappearance of the title compound of Example 246 step 2 in LC/MS. The crude reaction mixture was concentrated to about 10 mL of DMF. Upon addition of water to this DMF residue, a white solid was formed. This white solid was triturated in water for 20 min and filtered. The solid was collected, dissolved in THF, and dried with MgSO4. Removal of the solvent afforded a brown solid that was crystallized from CH3CN to give 2.1 g of the title compound as white needles (yield 73%). 1H NMR (300 MHz, d6-DMSO): 2.86-2.91 (m, 4H), 7.18 (d, 1H, J=1.2 Hz), 7.25 (s, 1H), 7.32-7.36 (m, 4H), 7.52-7.56 (m, 3H), 7.75 (s, 1H), 8.57 (s, 1H), 10.49 (s, 1H). M+1=497.

後処理

  1. customThe crude reaction mixture
  2. concentrationwas concentrated to about 10 mL of DMF
  3. additionUpon addition of water to this DMF residue
  4. customa white solid was formed
  5. customThis white solid was triturated in water for 20 min
  6. filtrationfiltered
  7. customThe solid was collected
  8. dissolutiondissolved in THF
  9. dry with materialdried with MgSO4
  10. customRemoval of the solvent
  11. customafforded a brown solid that
  12. customwas crystallized from CH3CN

出典と根拠

ORDレコード
ord-b26a430b7b7d4ac6a7fd2ec0979bd407
出典データセット
uspto-grants-2005_10
特許番号
US06956052B2

反応ノート

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