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Trifluoroacetic acid → (+/-)-trans-N-[(5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine trifluoroacetate

HRID 546414
Notes
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Reaction equation

HRID 546414 reaction equation
C(O[C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH2:15])=[O:7])(C)(C)C.[CH3:16][N:17]1[CH2:22][CH2:21][C:20]2[N:23]=[C:24](C([O-])=O)[S:25][C:19]=2[CH2:18]1.[Li+].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56]>CN(C)C=O.ClCCl>[F:53][C:54]([F:59])([F:58])[C:55]([OH:57])=[O:56].[CH3:16][N:17]1[CH2:22][CH2:21][C:20]2[N:23]=[C:24]([C:6]([NH:8][C@@H:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]3[NH2:15])=[O:7])[S:25][C:19]=2[CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 1514390(1R,2R)-trans-N-Boc-1,2-cyclohexanediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23704331Lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate

Product 1

HCID 18442875
(+/-)-trans-N-[(5-methyl-4,5,6,7-tetrahydrothiazolo-[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine trifluoroacetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(±)-trans-N-tert-Butoxycarbonyl-1,2-cyclohexane-diamine (642 mg) was dissolved in N,N-dimethylformamide (20 ml), and to the solution lithium 5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxylate (795 mg), 1-hydroxybenzotriazole monohydrate (46 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.30 g) were added, and the mixture was stirred overnight at room temperature. After the reaction mixture was concentrated under reduced pressure, and dichloromethane and water were added to the residue, the organic layer was taken out and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (dichloromethane:methanol 100:3) to obtain a pale yellow foamy substance. This substance was dissolved in dichloromethane (5 ml), and trifluoroacetic acid (30 ml) was added, and the mixture was stirred at room temperature for 1 minute. The reaction mixture was concentrated under reduced pressure to obtain the title compound (731 mg) as a pale brown foamy substance.

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure, and dichloromethane and water
  2. additionwere added to the residue
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (dichloromethane:methanol 100:3)
  6. customto obtain a pale yellow foamy substance
  7. stirringthe mixture was stirred at room temperature for 1 minute
  8. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5b5ea0ba79a4402f93c77d0a573e4e39
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07935824B2

Reaction notes

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