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Acetyl chloride → HCID 178474060, compound

HRID 2047567
Notes
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Reaction equation

HRID 2047567 reaction equation
[N:1]1([C@@H:7]2[CH2:10][C@H:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29]>ClCCl.O>[N:1]1([C@@H:7]2[CH2:10][C@H:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([NH:20][C:28](=[O:30])[CH3:29])[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 178507336HCID 178507336, compound

Product 1

HCID 178474060HCID 178474060, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The product of Example 101A (20 mg, 0.070 mmole) was dissolved in anhydrous dichloromethane (1.5 mL). To the solution was added triethylamine (35.6 mg, 49 μL, 0.35 mmole) and acetyl chloride (10 μL, 0.14 mmole). The mixture was stirred at room temperature overnight then diluted with water. The aqueous layer was extracted three times with dichloromethane and the combined organic layers were concentrated to give the crude product. The crude product was purified by column chromatography (0.5% ammonium hydroxide and 5% methanol in dichloromethane) to give the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 8.39 (d, J=2.14 Hz, 1H) 7.84 (d, J=8.54 Hz, 1H) 7.37 (s, 1H) 7.22 (dd, J=8.85, 2.14 Hz, 1H) 3.48-3.59 (m, 1H) 2.72-2.83 (m, 1H) 2.60-2.70 (m, 2H) 2.24-2.39 (m, 6H) 2.21 (s, 3H) 1.54-1.64 (m, 4H) 1.40-1.51 (m, 2H). MS: (M+H)+=330.

Workup

  1. extractionThe aqueous layer was extracted three times with dichloromethane
  2. concentrationthe combined organic layers were concentrated
  3. customto give the crude product
  4. customThe crude product was purified by column chromatography (0.5% ammonium hydroxide and 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-60ecd6334a434e289adee1b346abbfe2
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592467B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes