4-Toluenesulfonyl chloride → HCID 57657260, compound

HRID 244839Notes

Reaction equation

HRID 244839 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:28][CH2:29][CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][C:32]2=[O:36])[C:7]2[C:16]3[CH:15]=[C:14]([CH2:17][CH2:18][C:19]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:20])[CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:27]=1.ClC1C=C(C=CC=1)C(OO)=O.[OH-].[NH4+:49].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[NH2:49][C:9]1[C:8]2[N:27]=[C:5]([CH2:4][CH2:3][O:2][CH3:1])[N:6]([CH2:28][CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][C:32]3=[O:36])[C:7]=2[C:16]2[CH:15]=[C:14]([CH2:17][CH2:18][C:19]([N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[O:20])[CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69081539HCID 69081539, compound

Product 1

HCID 57657260HCID 57657260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of crude 1-{3-[2-(2-methoxyethyl)-8-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one, (0.85 g) in dichloromethane (75 mL) was added 3-chloroperoxybenzoic acid (60% pure, 500 mg, 1.91 mmol). After 18 hours concentrated ammonium hydroxide (50 mL) was added and the reaction was vigorously stirred for 10 minutes. p-Toluenesulfonyl chloride (690 mg, 3.60 mmol) was added in one portion and the mixture was stirred for one hour. The fractions were separated and aqueous fraction was extracted with chloroform (3×50 mL). The combined organic fractions were concentrated under reduced pressure. Purification by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a gradient of 0-30% CMA in chloroform) followed by recrystallization from acetonitrile provided 75 mg of 1-{3-[4-amino-2-(2-methoxyethyl)-8-(3-morpholin-4-yl-3-oxopropyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one as a pale yellow solid, mp 168-170° C.

Workup

  1. stirringthe mixture was stirred for one hour
  2. customThe fractions were separated
  3. extractionaqueous fraction was extracted with chloroform (3×50 mL)
  4. concentrationThe combined organic fractions were concentrated under reduced pressure
  5. customPurification by chromatography
  6. washeluting with a gradient of 0-30% CMA in chloroform)
  7. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-b790cb3c43ed45749184724cf8a166ee
Source dataset
uspto-grants-2014_02
Patent number
US08658666B2

Reaction notes

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