Furfurylamine → HCID 58820552, compound

HRID 458466Notes

Reaction equation

HRID 458466 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([C:28]2[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=2)=[C:8]2[C:12](=[CH:13][C:14]=1[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C@@H:11]1[CH2:24][CH2:25][CH2:26][N:10]1[C:9]2=[O:27])=[O:5])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:49]([NH2:55])[C:50]1[O:54][CH:53]=[CH:52][CH:51]=1>C1COCC1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][C:14]2[CH:13]=[C:12]3[C:8]([C:9](=[O:27])[N:10]4[CH2:26][CH2:25][CH2:24][C@H:11]43)=[C:7]([C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH:55][CH2:49][C:50]4[O:54][CH:53]=[CH:52][CH:51]=4)=[O:33])=[CH:35][CH:36]=3)[C:6]=2[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 3438FurfurylamineHCID 682631,1'-CarbonyldiimidazoleHCID 69742616HCID 69742616, compound

Product 1

HCID 58820552HCID 58820552, compoundYield 70,000%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 49 (241 mg, 0.49 mmol) and carbonyldimidazole (0.54 mmol, 88.2 mg) in THF (anhydrous, 15 ml) was stirred for 1 hr at r.t. Then was added dropwise a solution of furfurylamine (96.1 mg, 0.99 mmol) in THF (2 ml) and the mixture stirred at r.t. for 12 hr. Then the reaction mixture concentrated and the yellow oil purified on SiO2 (ethyl acetate:hexanes 1:5) to afford the title compound as a white solid (194 mg, 343 mmol): 1H NMR (400 MHz, d6-DMSO) δ 9.03 (t, 1H), 7.82 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.2 Hz, 2H), 7.26 (d, J=8.2 Hz, 2H), 7.20–7.17 (m, 2H), 7.09–7.04 (m, 2H), 6.36 (d, J=4.0 Hz, 1H), 6.25 (d, J=4.0 Hz, 1H), 4.69–4.65 (m, 1H), 4.46–4.44 (m, 2H), 3.91 (q, 2H), 3.39–3.36 (m, 1H), 3.19–3.13 (m, 1H), 2.90–2.79 (m, 4H), 2.28–2.18 (m, 3H), 1.13–1.08 (m, 1H), 1.08 (t, 3H) ppm. ESI-MS m/z 567 (M+H)+. HPLC (99%). Anal. calcd. for C34H31N2O5F 0.41H2O: C, 71.14; H, 5.59; N, 4.88. Found: C, 71.14; H, 5.66; N, 4.84.

Workup

  1. concentrationThen the reaction mixture concentrated
  2. customthe yellow oil purified on SiO2 (ethyl acetate:hexanes 1:5)

Sources & evidence

ORD record
ord-aae5cf823b594c04af1a0bd386386c29
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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