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Hydrochloric Acid → HCID 25064929、化合物

HRID 1513643
ノート
印刷プレビュー

反応式

HRID 1513643 の反応式
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([CH2:21][O:22][C:23]4[C:32]5[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=5)[N:26]=[CH:25][CH:24]=4)=[N:19][N:20]=3)[N:17]=2)[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].O.[OH-].[Li+].Cl.[CH3:39][O:40][CH2:41][CH2:42][NH2:43].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.FC1C=C(C2C=CC3N(C(COC4C5C(=CC(OC)=CC=5)N=CC=4)=NN=3)N=2)C=CC=1C(O)=O>C1COCC1.O.CO.CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([CH2:21][O:22][C:23]4[C:32]5[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=5)[N:26]=[CH:25][CH:24]=4)=[N:19][N:20]=3)[N:17]=2)[CH:9]=[CH:8][C:3]=1[C:4]([NH:43][CH2:42][CH2:41][O:40][CH3:39])=[O:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

12

反応物 7

HCID 313Hydrochloric AcidHCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 168937Lithium hydroxide, monohydrateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67503070Methyl 2-fluoro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)benzoate
HCID 675034182-Fluoro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)benzoic acid

生成物 1

HCID 25064929HCID 25064929、化合物

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

A mixture of methyl 2-fluoro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)benzoate (0.488 g, 1.06 mmol) (prepared according to General Method A) and lithium hydroxide hydrate (0.223 g, 5.31 mmol) in THF (20 mL), water (5 mL) and MeOH (5 mL) was heated to 40° C. for 3 h. Brought to near neutral pH with 1M HCl. Concentrated. Azeotroped with MeCN (20 mL) and PhMe (20 mL). Used without further purification. A mixture of 2-methoxyethylamine (0.033 ml, 0.38 mmol), HATU (0.24 g, 0.62 mmol), Hunig's Base (0.24 ml, 1.4 mmol), 2-fluoro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)benzoic acid (0.153 g, 0.34 mmol) in DMF was allowed to stir at room temperature for 1 h. Concentrated. Purified on RPHPLC. Took fractions containing product and made basic with 9% sodium carbonate. The volatiles were removed in vacuo and the product was isolated by filtration. Dried under vacuum. MS m/z=503.2 [M+1]+. Calc'd for C26H23FN6O4: 502.5.

後処理

  1. concentrationConcentrated
  2. customAzeotroped with MeCN (20 mL) and PhMe (20 mL)
  3. customUsed without further purification
  4. concentrationConcentrated
  5. customPurified on RPHPLC
  6. additionTook fractions containing product
  7. customThe volatiles were removed in vacuo
  8. customthe product was isolated by filtration
  9. customDried under vacuum

出典と根拠

ORDレコード
ord-7781293c1434450395dc241930976f6f
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08217177B2

反応ノート

読み込み中…

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