4-Amino-3-fluorobenzoic acid → 4-amino-N-(1-ethylpiperidin-4-yl)-3-fluorobenzamide

HRID 2234492

반응식

HRID 2234492 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]1.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>CC(N(C)C)=O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH3:20])[CH2:15][CH2:14]2)=[O:8])=[CH:4][C:3]=1[F:11]

참가 물질

6

반응물 4

HCID 99714-Amino-3-fluorobenzoic acidHCID 81531DiisopropylethylamineHCID 37349901-Ethylpiperidin-4-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 551027824-amino-N-(1-ethylpiperidin-4-yl)-3-fluorobenzamide수율 22.7%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

4-amino-3-fluorobenzoic acid (2.115 g, 13.6 mmol), 4-Amino-1-Ethyl Piperidine (Fluorochem; 1.923 g, 15 mmol), HATU (5.7 g, 15 mmol) and DIPEA (7.1 mL, 40.8 mmol) were combined in DMA (60 mL) and the resulting yellow solution stirred at room temperature for 20 minutes. The reaction was left over the weekend at room temperature, solvent evaporated and the residue dissolved in methanol (10 mL) and loaded onto an SCX-2 column (50 g) which pre-wet with MeOH (40 mL), flushed with MeOH (4×30 ml) and eluted with 7N ammonia in MeOH (4×30 mL). Product containing, ammoniacal fractions were combined to yield the title compound as a brown solid (0.819 g, 22%)

후처리

  1. waitThe reaction was left over the weekend at room temperature
  2. customsolvent evaporated
  3. dissolutionthe residue dissolved in methanol (10 mL)
  4. customflushed with MeOH (4×30 ml)
  5. washeluted with 7N ammonia in MeOH (4×30 mL)
  6. additionProduct containing

출처 및 근거

ORD 기록
ord-60cb88dc051744b899d25578ed6a4372
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709471B2

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