Benzoic Acid → HCID 15887544, compound

HRID 362540Notes

Reaction equation

HRID 362540 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[CH2:16][N:15]([C:17](=[O:26])[C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=3)[CH2:14][CH2:13][N:12]2[C:27](=[O:36])[CH2:28][NH:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:7]=[CH:8][C:9]=1[Cl:10].CCN(C(C)C)C(C)C.[C:46](O)(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[C:46]([N:33]1[CH2:32][CH2:31][CH:30]([NH:29][CH2:28][C:27]([N:12]2[CH2:13][CH2:14][N:15]([C:17](=[O:26])[C:18]3[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=3)[CH2:16][CH:11]2[C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=2)=[O:36])[CH2:35][CH2:34]1)(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9959862HCID 9959862, compound

Product 1

HCID 15887544HCID 15887544, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound obtained from Example 9 (0.23 g, 0.4 10 mmol) in CH2Cl2 (5 mL) was added Hunig's base (0.13 g, 1.0 mmol). This was followed by the addition of benzoic acid (49 mg, 0.4 mmol), HOBT (54 mg, 0.4 mmol), Et3N (40 mg, 0.4 mmol) and DEC (77 mg, 0.4 mmol) at 0° C. The solution was gradually warmed to RT and stirred overnight. After reaction was complete, the solution was diluted with CH2Cl2 (50 mL) and washed with saturated NaHCO3 solution (30 mL, 2×) and brine (20 mL, 3×). The organic layer was dried over MgSO4, filtered and concentrated to give crude material as an oil. The product was purified by chromatography on flash grade silica gel (50 g), eluting with 5% [NH4OH/MeOH (1:9)]/CH2Cl2 to give the title compound as a white solid (0.18 g), m.p. 94°-96° C.; FAB MS [M+1]+ 35 Cl 607.3.

Workup

  1. customAfter reaction
  2. washwashed with saturated NaHCO3 solution (30 mL, 2×) and brine (20 mL, 3×)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude material as an oil
  7. customThe product was purified by chromatography on flash grade silica gel (50 g)
  8. washeluting with 5% [NH4OH/MeOH (1:9)]/CH2Cl2

Sources & evidence

ORD record
ord-54f5c0cba23b4c6fb7b3cc739f8bb612
Source dataset
uspto-grants-1999_02
Patent number
US05869488

Reaction notes

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