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Hydrochloric Acid → HCID 25064929, 화합물

HRID 1511271
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HRID 1511271 반응식
[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]
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참가 물질

12

반응물 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

생성물 1

HCID 25064929HCID 25064929, 화합물

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
4 °C

실험 절차

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 4° 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.

후처리

  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

출처 및 근거

ORD 기록
ord-aeab43eb99624feb93556d391040c404
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08212041B2

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