Cyclohexylamine → HCID 136169029, compound

HRID 44446Notes

Reaction equation

HRID 44446 reaction equation
[OH:1][C:2]1[N:3]=[C:4]2[S:13][C:12]3[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=3[N:5]2[C:14](=[O:23])[C:15]=1[C:16]([NH:18][CH2:19][C:20]([OH:22])=O)=[O:17].C(N(CC)CC)C.[CH:31]1([NH2:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>ClCCl.CO>[CH:31]1([NH:37][C:20]([CH2:19][NH:18][C:16]([C:15]2[C:14](=[O:23])[N:5]3[C:6]4[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]=4[S:13][C:4]3=[N:3][C:2]=2[OH:1])=[O:17])=[O:22])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

8

Reactant 5

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1360089041293289-69-6HCID 178418300HCID 178418300, compound

Product 1

HCID 136169029HCID 136169029, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To the stirred suspension of [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid (0.70 gm, 0.0020 mole) in dichloromethane (20 ml), triethylamine (0.85 ml, 0.0062 mole) and cyclohexylamine (0.29 ml, 0.0025 mole) were added. To the reaction mixture, hydroxybenzotriazole (0.28 gm, 0.0020 mole) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.60 gm, 0.0031 mole) were added and stirred at room temperature for 12 hrs. Dichloromethane was distilled off and 1N hydrochloric acid (50 ml) was added to the residue, the separated solid was collected by filtration. The solid thus obtained was stirred in methanol (20 ml) at 60° C. for 0.5 hr, filtered and suck dried to give 0.60 gm title compound.

Workup

  1. additionwere added
  2. distillationDichloromethane was distilled off
  3. addition1N hydrochloric acid (50 ml) was added to the residue
  4. filtrationthe separated solid was collected by filtration
  5. customThe solid thus obtained
  6. filtrationfiltered
  7. customsuck dried

Sources & evidence

ORD record
ord-53ad18cf92a6496c8e32d1d38f5ee661
Source dataset
uspto-grants-2013_09
Patent number
US08541430B2

Reaction notes

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