Methanesulfonyl chloride → (+/-)-cis-N1-[(5-Chloroindol-2-yl)carbonyl]-N2-[[5-[2-(methanesulfonylamino)ethyl]-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl]carbonyl]-1,2-cyclohexane-diamine hydrochloride

HRID 546516Notes

Reaction equation

HRID 546516 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[N:11]=[C:12]([C:14]([NH:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][C@@H:18]3[NH:23][C:24]([C:26]3[NH:27][C:28]4[C:33]([CH:34]=3)=[CH:32][C:31]([Cl:35])=[CH:30][CH:29]=4)=[O:25])=[O:15])[S:13][C:7]=2[CH2:6]1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>N1C=CC=CC=1.Cl>[ClH:35].[Cl:35][C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[NH:27][C:26]([C:24]([NH:23][C@@H:18]1[CH2:19][CH2:20][CH2:21][CH2:22][C@@H:17]1[NH:16][C:14]([C:12]1[S:13][C:7]3[CH2:6][N:5]([CH2:4][CH2:3][NH:2][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:10][CH2:9][C:8]=3[N:11]=1)=[O:15])=[O:25])=[CH:34]2

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67056679HCID 67056679, compound

Product 1

HCID 68909334(+/-)-cis-N1-[(5-Chloroindol-2-yl)carbonyl]-N2-[[5-[2-(methanesulfonylamino)ethyl]-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl]carbonyl]-1,2-cyclohexane-diamine hydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

(±)-cis-N1-[[5-(2-Aminoethyl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl]carbonyl]-N2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine hydrochloride (110 mg) was dissolved in pyridine (3 ml), methanesulfonyl chloride (30 μl) was added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and a 85:15 mixed solvent of dichloromethane and methanol, and water were added to conduct liquid separation. The resultant organic layer was 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 product was suspended in 1N hydrochloric acid (0.3 ml), and the suspension was concentrated under reduced pressure to obtain the title compound (63 mg) as a pale yellow foamy substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona 85:15 mixed solvent of dichloromethane and methanol, and water were added
  3. customliquid separation
  4. dry with materialThe resultant organic layer was dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (dichloromethane:methanol=100:3)
  7. customto obtain a pale yellow foamy substance
  8. concentrationthe suspension was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f139d765ff414faab993309c16ad47a4
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

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