Benzoyl chloride → HCID 57961528, compound

HRID 541878Notes

Reaction equation

HRID 541878 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]([CH:23]=3)[CH2:12][NH:13][C:14]3[CH:22]=[C:18]([NH:19][C:20]=1[N:21]=2)[CH:17]=[CH:16][CH:15]=3.C(N(CC)CC)C.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C)C=O>[C:31]([N:13]1[CH2:12][C:11]2[CH:23]=[C:7]([CH:8]=[CH:9][CH:10]=2)[NH:6][C:5]2=[N:21][C:20](=[C:2]([Cl:1])[CH:3]=[N:4]2)[NH:19][C:18]2=[CH:22][C:14]1=[CH:15][CH:16]=[CH:17]2)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 57961661HCID 57961661, compound

Product 1

HCID 57961528HCID 57961528, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 6-chloro-2,4,8,14,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaene (20.0 mg, 0.0618 mmol) in N,N-dimethylformamide (0.24 mL) was added triethylamine (17.2 μL), followed by the addition of benzoyl chloride (17.4 mg, 0.12 mmol). The resultant solution was stirred at rt for 30 min. The mixture was quenched with H2O and concentrated. The residue was purified by silica gel column chromatography to give the desired product as an off-white powder (11 mg, 42%). LCMS for C24H19ClN5O (M+H)+: m/z=428.1. 1H NMR (300 MHz, DMSO-d6): δ 9.42 (s, 1H), 9.11 (s, 1H), 8.12 (s, 2H), 7.82 (s, 1H), 7.25 (m, 4H), 7.15 (m, 4H), 7.03 (m, 3H), 4.86 (m, 2H).

Workup

  1. customThe mixture was quenched with H2O
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22d592a723d5473689b868653d00c3cb
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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