Benzoyl chloride, 3-chloro- → HCID 178519571, compound

HRID 339304Notes

Reaction equation

HRID 339304 reaction equation
[N:1]1([CH2:8][C:9]2[NH:20][C:19]3[C:21]4[C:15]([C:16](=[O:22])[NH:17][N:18]=3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](Cl)=[O:28]>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([CH2:8][C:9]2[NH:20][C:19]3[C:21]4[C:15]([C:16](=[O:22])[NH:17][N:18]=3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH2:2][CH2:3]1)=[O:28]

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 178518773HCID 178518773, compound2×

Product 1

HCID 178519571HCID 178519571, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized from compound 26. To a solution of compound 26 (0.2 g, 0.6 mmol) in 5 mL of CH2Cl2 was added 1 mmol of TEA and 0.8 mmol of 3-chloro-benzoyl chloride. The reaction was stirred overnight at room temperature. After the solvents were evaporated, the residue was purified with semi-preparative HPLC to afford a solid (16% yield). MP: 147-149° C.; MS (ES−): 436; 1H NMR (400 MHz, CDCl3): 1.88-2.08 (m, 2H), 2.86-3.07 (m, 4H), 3.52-3.71 (m, 4H), 3.81-3.89 (m, 2H), 7.33-7.43 (m, 4H), 7.62 (d, 1H), 7.81 (t, 1H), 7.90 (t, 1H). Anal. Calcd. for C22H21ClN6O2.0.7H2O: C, 54.89; H, 4.39; N, 16.70. Found: C, 54.93; H, 4.43; N, 16.34.

Workup

  1. customAfter the solvents were evaporated
  2. customthe residue was purified with semi-preparative HPLC

Sources & evidence

ORD record
ord-163400c9716a44c08c3fa8f2ee114521
Source dataset
uspto-grants-2014_11
Patent number
US08894989B2

Reaction notes

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