N-methyl-2-pyrrolidone → 4-(2-Hydroxy-2-methylpropylamino)benzene-sulfonic acid 2-[(piperidine-4-carbonyl)amino]benzothiazol-6-yl ester

HRID 1867956Notes

Reaction equation

HRID 1867956 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([O:19][S:20]([C:23]4[CH:28]=[CH:27][C:26](F)=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[O:8])[CH2:3][CH2:2]1.[N:30]1C=C[CH:33]=[C:32]([C:36]2N=CN(CCCCN)C=2)[CH:31]=1.CN1C(=[O:52])CCC1>>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([O:19][S:20]([C:23]4[CH:28]=[CH:27][C:26]([NH:30][CH2:31][C:32]([OH:52])([CH3:36])[CH3:33])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 110421604-(4-(Pyridin-3-yl)-1H-imidazol-1-yl)butan-1-amineHCID 579808454-Fluorobenzenesulfonic 2-[(piperidine-4-carbonyl)amino]-benzothiazol-6-yl ester2×

Product 1

HCID 114970604-(2-Hydroxy-2-methylpropylamino)benzene-sulfonic acid 2-[(piperidine-4-carbonyl)amino]benzothiazol-6-yl ester

Procedure

A solution of 4-fluorobenzenesulfonic 2-[(piperidine-4-carbonyl)amino]benzo-thiazol-6-yl ester (intermediate 4) (50 mg, 0.114 mmol) and of 4-(4-pyrid-3-yl-imidazol-1-yl)butylamine (40.93 mg, 0.459 mmol) in 0.5 ml of NMP is heated at 130° C. by microwave for 5 minutes. The crude reaction product is purified by preparative LC/MS (basic medium (pH 9)) to give after freeze-drying 21 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic 2-(cyclo-propanecarbonylamino)benzothiazol-6-yl ester (pale yellow solid).

Workup

  1. customThe crude reaction product
  2. customis purified by preparative LC/MS (basic medium (pH 9))
  3. customto give
  4. dry with materialafter freeze-drying 21 mg of 4-(2-hydroxy-2-methylpropylamino)benzenesulfonic 2-(cyclo-propanecarbonylamino)benzothiazol-6-yl ester (pale yellow solid)

Sources & evidence

ORD record
ord-e0e208052fce482aad1c5dffba83f802
Source dataset
uspto-grants-2009_12
Patent number
US07632952B2

Reaction notes

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