Ethoxyacetyl chloride → HCID 86626165, compound

HRID 2383149Notes

Reaction equation

HRID 2383149 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=2)[N:16]=[CH:15][C:14]=1[NH2:31])([CH3:4])([CH3:3])[CH3:2].C(OC(=O)NCCCCNC1C2C(=[CH:50][C:51]([O:55][CH2:56][C:57]3C=CC=CC=3)=CC=2)N=CC=1N)(C)(C)C.C(OCC(Cl)=O)C.COCCC(Cl)=O>>[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[C:13]2[C:22]3[CH:21]=[C:20]([O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:19]=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:31]=[C:50]1[CH2:51][O:55][CH2:56][CH3:57])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 84189Ethoxyacetyl chlorideHCID 27597283-Methoxypropanoyl chlorideHCID 68900070Tert-butyl [4-(3-amino-7-benzyloxyquinolin-4-ylamino)butyl]carbamateHCID 86626163HCID 86626163, compound

Product 1

HCID 86626165HCID 86626165, compound

Procedure

For Example 73, a modification of the general method described for Part C of Example 50 was followed using tert-butyl{4-[3-amino-6-(benzyloxy)quinolin-4-ylamino]butyl}carbamate (9.25 g, 21.2 mmol) in lieu of tert-butyl{4-[3-amino-7-(benzyloxy)quinolin-4-ylamino]butyl}carbamate and ethoxyacetyl chloride (2.86 g, 23.3 mmol) in lieu of methoxypropionyl chloride. After the cyclization reaction, the solvent was removed under reduced pressure, and the residue was dissolved in chloroform (400 mL). The resulting solution was washed with water (2×200 mL) and brine (1×200 mL), concentrated under reduced pressure, and dried under high vacuum to provide a brown oil. The crude product was purified by column chromatography on silica gel (400 g, eluting with 95:5 dichloromethane:methanol). The resulting solid was triturated with diethyl ether and isolated by filtration to provide 5.37 g of tert-butyl{4-(8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate as an off-white powder.

Workup

  1. customAfter the cyclization reaction
  2. customthe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (400 mL)
  4. washThe resulting solution was washed with water (2×200 mL) and brine (1×200 mL)
  5. concentrationconcentrated under reduced pressure
  6. customdried under high vacuum
  7. customto provide a brown oil
  8. customThe crude product was purified by column chromatography on silica gel (400 g, eluting with 95:5 dichloromethane:methanol)
  9. customThe resulting solid was triturated with diethyl ether
  10. customisolated by filtration

Sources & evidence

ORD record
ord-dc8a274ba642455da0858f0fb5fe2118
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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