Hydrochloric Acid → HCID 59295090, compound

HRID 2233068Notes

Reaction equation

HRID 2233068 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]3[C:14]([C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=4)=[N:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[NH:18][C:5]3=[CH:4][C:3]1=2.N1C=CC=CC=1.[C:39](Cl)(=[O:41])[CH3:40].Cl>C(Cl)Cl>[C:39]([N:18]1[C:5]2[C:6](=[CH:7][C:8]3[C:9]([CH3:12])([CH3:13])[CH2:10][CH2:11][C:2]([CH3:32])([CH3:1])[C:3]=3[CH:4]=2)[C:14]([C:23]2[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:30][CH:31]=2)=[N:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]1=2)(=[O:41])[CH3:40]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 59295097HCID 59295097, compound

Product 1

HCID 59295090HCID 59295090, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution 4-(7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-5,13-diazabenzo[4,5]-cyclohepta[1,2-b]naphthalen-12-yl)benzoic acid (27) (0.47 mmol) and pyridine (1.2 mmol) in CH2Cl2 (4 mL) is treated with acetyl chloride (1.0 mmol) and stirred at room temperature for 6 h. The mixture is poured into 1 N HCl and extracted with EtOAc. The extract is washed with brine, dried over MgSO4 and evaporated in vacuo. The resulting solid is purified by reversed-phase HPLC (0.1% TFA, 30-100% gradient CH3CN) to give the acid (29).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract is washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe resulting solid is purified by reversed-phase HPLC (0.1% TFA, 30-100% gradient CH3CN)

Sources & evidence

ORD record
ord-3344c61c20664897a061ef2371e4833b
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

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