Hydrochloric Acid → HCID 59188716, compound

HRID 2090518Notes

Reaction equation

HRID 2090518 reaction equation
[F:1][C:2]([F:37])([C:6]([F:36])([F:35])[C:7]([F:34])([F:33])[C:8]([F:32])([F:31])[C:9]([F:30])([F:29])[C:10]([F:28])([F:27])[C:11]([F:26])([F:25])[C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[C:3](Cl)=[O:4].[OH:38][C:39]1[CH:81]=[CH:80][C:42]([C:43]2[CH:48]=[CH:47][C:46]([C:49]3[C:62]4[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=4)[C:56]4[CH:55]=[CH:54][C:53]([C:74]5[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=5)([C:63]5[CH:68]=[CH:67][C:66]([N:69]6[CH2:73][CH2:72][CH2:71][CH2:70]6)=[CH:65][CH:64]=5)[O:52][C:51]=4[CH:50]=3)=[CH:45][CH:44]=2)=[CH:41][CH:40]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:1][C:2]([F:37])([C:6]([F:36])([F:35])[C:7]([F:34])([F:33])[C:8]([F:32])([F:31])[C:9]([F:30])([F:29])[C:10]([F:28])([F:27])[C:11]([F:26])([F:25])[C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[C:3]([O:38][C:39]1[CH:40]=[CH:41][C:42]([C:43]2[CH:44]=[CH:45][C:46]([C:49]3[C:62]4[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=4)[C:56]4[CH:55]=[CH:54][C:53]([C:74]5[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=5)([C:63]5[CH:68]=[CH:67][C:66]([N:69]6[CH2:73][CH2:72][CH2:71][CH2:70]6)=[CH:65][CH:64]=5)[O:52][C:51]=4[CH:50]=3)=[CH:47][CH:48]=2)=[CH:80][CH:81]=1)=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 70862872HCID 70862872, compoundHCID 87495264HCID 87495264, compound

Product 1

HCID 59188716HCID 59188716, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Solid 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-tricosafluorododecanoyl chloride (0.37 g, 0.58 mmol) was added to a solution of 6-[4′-(hydroxy)biphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[2,1-b]pyran (0.33 g, 0.58 mmol) in DCM (100 mL) containing 4-dimethylaminopyridine (0.05 g) and pyridine (2 mL) under N2 with stirring. The mixture was stirred at room temperature for 3 h, poured into HCl (2 M, 100 mL), extracted with EtOAc (3×30 mL), washed with water (100 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (60% in hexanes as eluent), the solvent removed under reduced pressure. Hexane was added and the resulting solid filtered to give the title compound (0.31 g, 46%) as a colourless powder, mp 129-130° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. extractionextracted with EtOAc (3×30 mL)
  3. washwashed with water (100 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. filtrationThe residue was filtered through a short plug of silica
  7. customthe solvent removed under reduced pressure
  8. additionHexane was added
  9. filtrationthe resulting solid filtered

Sources & evidence

ORD record
ord-147ceb94df6d4f1fac35fecaf3a0b04e
Source dataset
uspto-grants-2013_05
Patent number
US08436184B2

Reaction notes

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