Water → HCID 10312048, compound

HRID 458410Notes

Reaction equation

HRID 458410 reaction equation
CCN=C=NCCCN(C)C.[CH2:12]([NH2:18])[C:13]1[O:17][CH:16]=[CH:15][CH:14]=1.[CH2:19]([O:21][C:22]([C:24]1[C:25]([C:46]2[CH:54]=[CH:53][C:49]([C:50](O)=[O:51])=[CH:48][CH:47]=2)=[C:26]2[C:41](=[O:42])[N:40]3[CH2:43][CH2:44][CH2:45][N:39]3[C:27]2=[N:28][C:29]=1[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)=[O:23])[CH3:20].C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C>[F:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][CH2:30][C:29]2[N:28]=[C:27]3[N:39]4[CH2:45][CH2:44][CH2:43][N:40]4[C:41](=[O:42])[C:26]3=[C:25]([C:46]3[CH:54]=[CH:53][C:49]([C:50]([NH:18][CH2:12][C:13]4[O:17][CH:16]=[CH:15][CH:14]=4)=[O:51])=[CH:48][CH:47]=3)[C:24]=2[C:22]([O:21][CH2:19][CH3:20])=[O:23])=[CH:33][CH:34]=1

Participants

7

Reactant 5

HCID 962WaterHCID 3438FurfurylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11225567HCID 11225567, compound

Product 1

HCID 10312048HCID 10312048, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDCI (31 mg, 0.16 mmol) was added to a solution of furfuryl amine (14 mg, 0.15 mmol), the product from Step E (71 mg, 0.15 mmol) and HOBT.H2O (20 mg, 0.15 mmol) in DMF (2.5 mL). The reaction was stirred 4 h at rt and then concentrated at reduced pressure. The remaining material was dissolved in CH2Cl2, washed with water, dried, filtered and concentrated. Chromatography on silica gel afforded the title compound as a yellow solid (30 mg, 0.05 mmol, 33%): 1H NMR (400 MHz, DMSO-d6) δ 9.06 (t, 1H, J=6), 7.89 (d, 2H, J=8), 7.56 (br s, 1H), 7.38 (d, 2H, J=8), 7.22 (br t, 2H J˜8), 7.07 (t, 2H, J=9), 6.37 (br s, 1H), 6.26 (d, 1H, J=3), 4.46 (d, 2H, J=6), 3.90 (m, 4H), 3.77 (t, 2H, J=7), 3.06 (m, 2H), 2.99 (m, 2H), 2.54 (quint., 2H, J=7), 0.78 (t, 3H, J=7) ppm; ESI-MS m/z 569 (M+H)+;

Workup

  1. concentrationconcentrated at reduced pressure
  2. dissolutionThe remaining material was dissolved in CH2Cl2
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e770f28b2f434e0aa274670de69eb6b0
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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