Acetyl chloride → HCID 10461651, compound

HRID 900159Notes

Reaction equation

HRID 900159 reaction equation
[NH2:1][C:2]1[CH:41]=[CH:40][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([N:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][O:27][C:28]4[CH:29]=[CH:30][CH:31]=[C:32]5[C:37]=4[N:36]=[C:35]([CH3:38])[CH:34]=[CH:33]5)[C:20]=3[Cl:39])[CH3:18])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:51](Cl)(=[O:53])[CH3:52]>C(#N)C>[C:51]([NH:1][C:2]1[CH:41]=[CH:40][C:5]([C:6]([C:8]2[N:12]([CH3:13])[C:11]([CH2:14][C:15]([N:17]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH2:26][O:27][C:28]4[CH:29]=[CH:30][CH:31]=[C:32]5[C:37]=4[N:36]=[C:35]([CH3:38])[CH:34]=[CH:33]5)[C:20]=3[Cl:39])[CH3:18])=[O:16])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)(=[O:53])[CH3:52]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 22288562HCID 22288562, compound

Product 1

HCID 10461651HCID 10461651, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 56 (0.033 g, 0.056 mmol) was dissolved in 5 mL acetonitrile. To this was added diisopropylethylamine (0.032 mL, 0.184 mmol) and acetyl chloride (0.05 mL, 0.703 mmol). The reaction was allowed to stir for 2 hours then was quenched with the addition of ˜2 ml of methanol. The solvents were evaporated and the residue purified via reverse phase chromatography eluting with a gradient of acetonitrile:water 10-90%.The proper fractions were isolated and the solvents were lyophilized to yield the product (0.021 g, 0.028 mmol) as an off-white powder. 1H NMR (CDCl3): δ 8.61 (d, 1H), 7.84-7.47 (m, 9H), 7.37 (d, 1H), 6.55 (d, 1H), 5.86 (d, 1H), 5.60 (s, 2H), 3.84 (s, 3H), 3.53 (m, 2H), 3.28 (s, 3H), 2.93 (s, 3H), 2.21 (s, 3H); MS: M+1=629.

Workup

  1. customthen was quenched with the addition of ˜2 ml of methanol
  2. customThe solvents were evaporated
  3. customthe residue purified via reverse phase chromatography
  4. washeluting with a gradient of acetonitrile
  5. customThe proper fractions were isolated

Sources & evidence

ORD record
ord-ac35ce88b0eb43d2bc1b1e84ebb0f34c
Source dataset
uspto-grants-2008_04
Patent number
US07358261B2

Reaction notes

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