Ethoxyacetyl chloride → tert-butyl{4-(8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate

HRID 598321노트

반응식

HRID 598321 반응식
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][C:8]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[CH:7][CH:6]=2.NC1C=NC2C(C=1NCCCCNC(=O)OC(C)(C)C)=CC=[C:39]([O:57][CH2:58][C:59]1C=CC=CC=1)[CH:38]=2.C(OCC(Cl)=O)C.COCCC(Cl)=O>>[CH2:26]([O:25][C:8]1[CH:7]=[CH:6][C:5]2[N:4]=[CH:3][C:2]3[N:1]=[C:38]([CH2:39][O:57][CH2:58][CH3:59])[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:11]=3[C:10]=2[CH:9]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

5

반응물 4

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

생성물 1

HCID 86626165tert-butyl{4-(8-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl]butyl}carbamate

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d8d9bddb753349038fb2ac6c00b85453
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897597B2

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