6-Chloro-2-benzothiazolamine → HCID 12093897, compound

HRID 2120168Notes

Reaction equation

HRID 2120168 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15]3[C:20]([C:21]([O-:23])=O)=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[NH4+].S(Cl)(Cl)=O.[NH2:29][C:30]1[S:31][C:32]2[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:33]=2[N:34]=1>C(Cl)Cl.N1C=CC=CC=1>[Cl:39][C:37]1[CH:36]=[CH:35][C:33]2[N:34]=[C:30]([NH:29][C:21]([C:20]3[C:15]([NH:14][CH2:13][CH:10]4[CH2:9][CH2:8][N:7]([C:4]5[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=5)[CH2:12][CH2:11]4)=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:23])[S:31][C:32]=2[CH:38]=1

Participants

6

Reactant 3

HCID 72266-Chloro-2-benzothiazolamineHCID 24386Thionyl ChlorideHCID 11174879Ammonium 2-[[1-(4-pyridinyl)piperidin-4-ylmethyl]amino]pyridine-3-carboxylate

Product 1

HCID 12093897HCID 12093897, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ammonium 2-[[1-(4-pyridinyl)piperidin-4-ylmethyl]amino]pyridine-3-carboxylate (400 mg, 1.28 mmol) in methylene chloride (5 mL) was treated with thionyl chloride (0.112 mL, 1.54 mmol) and the mixture was heated at reflux. After 3 h, the mixture was cooled and then treated dropwise with a solution of 2-amino-6-chlorobenzothiazole (284 mg, 1.54 mmol) in pyridine (5 mL). After 1 h, the mixture was concentrated in the presence of silica gel. The residue was purified by column chromatography (SiO2: 1 to 4% [2 N ammonia in methanol]:chloroform) followed by recrystallization from methanol to yield 68 mg (11%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. temperaturethe mixture was cooled
  4. waitAfter 1 h
  5. concentrationthe mixture was concentrated in the presence of silica gel
  6. customThe residue was purified by column chromatography (SiO2: 1 to 4% [2 N ammonia in methanol]:chloroform)
  7. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-6a7e3735d29a4c47bb1dbd91ec3431ee
Source dataset
uspto-grants-2004_02
Patent number
US06689780B1

Reaction notes

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