Benzeneacetic acid, 2-fluoro- → HCID 44218725, compound

HRID 1931502Notes

Reaction equation

HRID 1931502 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC.[F:43][B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.F[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=1[CH2:72][C:73]([OH:75])=O>O1CCCC1.O>[F:43][C:70]1[CH:69]=[CH:68][C:67]([CH2:72][C:73]([NH:21][C:16]2[CH:17]=[C:18]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([NH:10][C@H:1]2[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]2)[CH:20]=[CH:19]3)=[O:75])=[CH:66][CH:71]=1

Participants

8

Reactant 5

HCID 67979Benzeneacetic acid, 2-fluoro-HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

Product 1

HCID 44218725HCID 44218725, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(R)—N2-indan-1-yl-quinoline-2,6-diamine (0.05 g, 0.18 mmol), ethyldiisopropylamine (0.068 mL, 0.4 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC-HCl, 0.038 mg, 0.2 mmol), 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (HOBt, 0.027 mg, 0.2 mmol) and 2-fluorophenyl acetic acid (0.031 mg, 0.2 mmol) were dissolved in tetrahydrofurane (3.0 mL). The reaction mixture was stirred at ambient temperature for 3 h. Then it was diluted with water and extracted with ethyl acetate (3×). The combined organic phases were dried on sodium sulfate and evaporated. The crude product was purified by column chromatography (silica gel, heptane, ethyl acetate 4:1/1:1). The title compound (0.025 g, 33%) was obtained as an off-white solid; MS: m/e=412.6 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. customThe combined organic phases were dried on sodium sulfate
  3. customevaporated
  4. customThe crude product was purified by column chromatography (silica gel, heptane, ethyl acetate 4:1/1:1)

Sources & evidence

ORD record
ord-3d749968323f4a059b1bc7c7d13f6944
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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