Triethylamine → HCID 69078363, compound

HRID 1907962Notes

Reaction equation

HRID 1907962 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].[NH2:6][O:7][CH2:8][C:9]1[N:10]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]2[C:20]3[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=3[N:14]=[C:13]([NH2:21])[C:12]=2[N:22]=1.C(N(CC)CC)C>ClCCl>[ClH:5].[NH2:21][C:13]1[C:12]2[N:22]=[C:9]([CH2:8][O:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:10]([CH2:23][CH:24]([CH3:25])[CH3:26])[C:11]=2[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 11289248HCID 11289248, compound

Product 1

HCID 69078363HCID 69078363, compoundYield 13.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methanesulfonyl chloride (0.253 mL, 3.27 mmol) in dichloromethane (10 mL) was added dropwise to a stirred solution of 2-[(aminooxy)methyl]-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 123, 860 mg, 2.97 mmol) and triethylamine (1.24 mL, 8.92 mmol) in dichloromethane (20 mL) at 0° C. After 1 hour, additional methanesulfonyl chloride (0.125 mL in dichloromethane (5 mL)) and triethylamine (0.5 mL) were added. The reaction mixture was stirred for an additional 30 minutes, then was concentrated under reduced pressure to afford a yellow foam. The foam was purified by chromatography using a HORIZON HPFC system (silica gel, gradient elution with 5-15% 1 M NH3 in methanol/dichloromethane) followed by crystallization from methanol/acetonitrile. The crystals were isolated by filtration, washed with acetonitrile, and dried in a vacuum oven to yield 160 mg of N-{[4-amino-1-(2-methylpropyl)-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-2-yl]methoxy}methanesulfonamide hydrochloride as a white crystals, mp 211-213° C.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto afford a yellow foam
  3. customThe foam was purified by chromatography
  4. washa HORIZON HPFC system (silica gel, gradient elution with 5-15% 1 M NH3 in methanol/dichloromethane)
  5. customfollowed by crystallization from methanol/acetonitrile
  6. customThe crystals were isolated by filtration
  7. washwashed with acetonitrile
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6698e3d1e5a7480eaef74e9488e6bb07
Source dataset
uspto-grants-2013_12
Patent number
US08598192B2

Reaction notes

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