Dichloromethane → HCID 67052505, compound

HRID 599461Notes

Reaction equation

HRID 599461 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:25]Cl)[N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:5][C:4]=2[N:3]=1.[OH:35][N:36]1[C:40](=[O:41])[C:39]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:38]2[C:37]1=[O:46].C(N(CC)CC)C.ClCCl>CN(C=O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:35][N:36]3[C:40](=[O:41])[C:39]4[C:38](=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:37]3=[O:46])[N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 67052394HCID 67052394, compound

Product 1

HCID 67052505HCID 67052505, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of tert-butyl 2-[4-amino-7-(benzyloxy)-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate (2.70 g, 5.60 mmol) in DMF (10 mL) was added to a stirred solution of N-hydroxyphthalimide (1.10 g, 6.72 mmol) and triethylamine (1.56 mL, 11.2 mmol) in DMF (10 mL) at room temperature. A solid formed after 10 minutes. After 1.5 hours, dichloromethane (50 mL) was added and the solid was isolated by filtration, washed with dichloromethane followed by diethyl ether, and dried under vacuum to yield 3.15 g of tert-butyl 2-(4-amino-7-(benzyloxy)-2-{[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]methyl}-1H-imidazo[4,5-c]quinolin-1-yl)ethylcarbamate as an off-white solid.

Workup

  1. customA solid formed after 10 minutes
  2. customthe solid was isolated by filtration
  3. washwashed with dichloromethane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-cb53fe71a25a451293c55955a7e6e44c
Source dataset
uspto-grants-2011_03
Patent number
US07897767B2

Reaction notes

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