N-Cyclohexyl-4-[(2-methylprop-2-en-1-yl)oxy]cyclohexan-1-amine → HCID 178450579, compound

HRID 731455Notes

Reaction equation

HRID 731455 reaction equation
C1(N([C@H]2CC[C@H](OC)CC2)C(=O)NC2SC(SCC(O)=O)=CN=2)CCCC1.O[C@H]1CC[C@H](N2C(=O)C3C(=CC=CC=3)C2=O)CC1.C1(=O)CCCCCC1.BrCC(C)=C.C(OC(=O)C(SC1SC(N)=NC=1)C)C.[CH:73]1([NH:79][C@H:80]2[CH2:85][CH2:84][C@H:83]([O:86][CH2:87][C:88]([CH3:90])=[CH2:89])[CH2:82][CH2:81]2)[CH2:78][CH2:77][CH2:76][CH2:75][CH2:74]1.C1(NC2CCC(OCC(C)=C)CC2)CCCCC1>CC(O)=O>[CH:73]1([NH:79][C@H:80]2[CH2:85][CH2:84][C@H:83]([O:86][CH2:87][CH:88]([CH3:90])[CH3:89])[CH2:82][CH2:81]2)[CH2:74][CH2:75][CH2:76][CH2:77][CH2:78]1

Participants

8

Reactant 6

HCID 67483354N-Cyclohexyl-4-[(2-methylprop-2-en-1-yl)oxy]cyclohexan-1-amineHCID 67483452HCID 67483452, compoundHCID 86610213(2-Aminothiazole-5-ylsulfanyl)-propionic acid ethyl esterHCID 178450578HCID 178450578, compoundHCID 178496618HCID 178496618, compoundHCID 178515017HCID 178515017, compound

Product 1

HCID 178450579HCID 178450579, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to the procedure for the synthesis of {2-[3-cyclopentyl-3-(trans-4-methoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid using 2-(trans-4-hydroxy-cyclohexyl)-isoindole-1,3-dione, 3-bromo-2-methylpropene cycloheptanone and 2-(2-amino-thiazol-5-ylsulfanyl)-2-methyl-acetic acid ethyl ester. The intermediate cyclohexyl-[trans-4-(2-methyl-allyloxy)-cyclohexyl]-amine was hydrogenated using the following procedure: Cyclo-hexyl-[4-(2-methyl-allyloxy)-cyclohexyl]-amine (540 mg, 2.15 mmol) was dissolved in 10 mL AcOH and the setup was flushed with N2 before 50 mg Pd/C was added. A balloon was charged with N2 and connected to the setup. The reaction mixture was stirred for three days at room temperature before the Pd was filtered off using a pad of celite. The filtrate was poured on 1 N NaOH (pH>12) and the mixture was extracted 3× with diethylether (50 mL), and dried (MgSO4) to give cyclohexyl-(trans-4-isobutoxy-cyclohexyl)-amine which was trans-formed to the title compound according to the procedure for the synthesis of {2-[3-cyclopentyl-3-(trans-4-methoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid.

Workup

  1. customPrepared
  2. customthe setup was flushed with N2 before 50 mg Pd/C
  3. additionwas added
  4. additionA balloon was charged with N2
  5. filtrationwas filtered off
  6. additionThe filtrate was poured on 1 N NaOH (pH>12)
  7. extractionthe mixture was extracted 3× with diethylether (50 mL)
  8. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-0f5116543f7a47ca93fd1e575b3f4651
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

Loading…