Cyclohexanecarboxylic acid → N-(6-bromobenzo[d]thiazol-2-yl)cyclohexanecarboxamide

HRID 2077601

Reaction equation

HRID 2077601 reaction equation
CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:34]1([C:40]([OH:42])=O)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.[Br:43][C:44]1[CH:53]=[CH:52][C:47]2[N:48]=[C:49]([NH2:51])[S:50][C:46]=2[CH:45]=1>C(Cl)Cl>[Br:43][C:44]1[CH:53]=[CH:52][C:47]2[N:48]=[C:49]([NH:51][C:40]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]3)=[O:42])[S:50][C:46]=2[CH:45]=1

Participants

6

Reactant 4

HCID 7413Cyclohexanecarboxylic acidHCID 81531DiisopropylethylamineHCID 851492-Benzothiazolamine, 6-bromo-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 4604615N-(6-bromobenzo[d]thiazol-2-yl)cyclohexanecarboxamideYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Hunig's base (286 μl, 1637 μmol), HATU (830 mg, 2182 μmol) and cyclohexanecarboxylic acid (147 mg, 1146 μmol) was dissolved in 2.0 mL CH2Cl2 and stirred at room temperature for 10 min. 6-bromobenzo[d]thiazol-2-amine (250 mg, 1091 μmol) was added, and stirring was continued overnight. The solids were filtered and washed with CH2Cl2. The filtrate was concentrated, dissolved in CH2Cl2 and purified by silica gel chromatography using 100% CH2Cl2 to provide N-(6-bromobenzo[d]thiazol-2-yl)cyclohexanecarboxamide (290 mg, 78% yield) as a white solid. MS (ESI pos. ion) m/z calc'd for C14H15BrN2OS: 339.3/341.3. found 339.0/341.0.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. filtrationThe solids were filtered
  4. washwashed with CH2Cl2
  5. concentrationThe filtrate was concentrated
  6. dissolutiondissolved in CH2Cl2
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-9ed56c1abbf44a52bf197a3bc1952a2c
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Linked notes

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