9-Carboxyfluorene → HCID 178512314, compound

HRID 1383445Notes

Reaction equation

HRID 1383445 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][NH:7][C:8]([NH:20][C:21]#[N:22])=[N:9][C:10]2[CH:19]=[CH:18]C=[C:16]3[C:11]=2C=CC=[N:15]3)=[CH:4][CH:3]=1.[CH:25]1[C:37]2[CH:36]([C:38](O)=[O:39])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]=2[CH:28]=[CH:27][CH:26]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[C:21]([N:20]=[C:8]([NH:9][C:10]1[CH:11]=[CH:16][N:15]=[CH:18][CH:19]=1)[NH:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:38]([CH:36]2[C:37]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[C:30]3[C:35]2=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:39])=[CH:24][CH:23]=1)#[N:22]

Participants

7

Reactant 4

HCID 748099-CarboxyfluoreneHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178512242HCID 178512242, compound

Product 1

HCID 178512314HCID 178512314, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(4-Amino-benzyl)-N′-cyano-N″-quinolin-5-yl-guanidine (133 mg, 0.50 mmol) and 9H-fluorene-9-carboxylic acid (105 mg, 0.50 mmol) were suspended in N,N-dimethylformamide(1.0 mL). Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (232 mg, 0.52 mmol) was added followed by N,N-diisopropylethylamine (0.20 mL, 1.15 mmol). The reaction mixture was stirred at room temperature for 24 hours and then diluted with ethyl acetate (30 mL). This solution was washed with water (30 mL×2) and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give the desired product (102 mg, 44.5%). 1H NMR (DMSO-d6, ppm): 10.72 (s, 1H), 9.59 (bs, 1H), 8.37 (d, 2H), 8.27 (bs, 1H), 7.90 (d, 2H), 7.60 (t, 4H), 7.43 (t, 2H), 7.31 (m, 4H), 7.18 (m, 2H), 5.03 (s, 1H), 4.43 (d, 2H).

Workup

  1. washThis solution was washed with water (30 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8f4b072187f94d54b216d661d3e09555
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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