Piperidine → HCID 178473850, compound

HRID 731417Notes

Reaction equation

HRID 731417 reaction equation
C[C@H]1CC[C@H](N[CH:9]2[CH2:14][CH2:13][N:12](C(=O)C)[CH2:11][CH2:10]2)CC1.C(OC(=O)CSC1SC(N)=NC=1)C.[C:31]([N:34]1[CH2:39][CH2:38][CH:37]([N:40]([C@H:54]2[CH2:59][CH2:58][C@H:57]([CH3:60])[CH2:56][CH2:55]2)[C:41](=[O:53])[NH:42][C:43]2[S:44][C:45]([S:48][CH2:49][C:50]([OH:52])=[O:51])=[CH:46][N:47]=2)[CH2:36][CH2:35]1)(=[O:33])[CH3:32].C1C=C2C(N(O)N=NC2=CC=1)=O.CCN=C=NCCCN(C)C.N1CCCCC1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:31]([N:34]1[CH2:35][CH2:36][CH:37]([N:40]([C@H:54]2[CH2:59][CH2:58][C@H:57]([CH3:60])[CH2:56][CH2:55]2)[C:41](=[O:53])[NH:42][C:43]2[S:44][C:45]([S:48][CH2:49][C:50]([OH:52])=[O:51])=[CH:46][N:47]=2)[CH2:38][CH2:39]1)(=[O:33])[CH3:32].[C:31]([N:34]1[CH2:39][CH2:38][CH:37]([N:40]([C@H:54]2[CH2:59][CH2:58][C@H:57]([CH3:60])[CH2:56][CH2:55]2)[C:41]([NH:42][C:43]2[S:44][C:45]([S:48][CH2:49][C:50](=[O:52])[N:12]3[CH2:13][CH2:14][CH2:9][CH2:10][CH2:11]3)=[CH:46][N:47]=2)=[O:53])[CH2:36][CH2:35]1)(=[O:33])[CH3:32]

Participants

10

Reactant 7

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 81531DiisopropylethylamineHCID 21455623Ethyl 2-(2-aminothiazol-5-ylthio)acetateHCID 178473841HCID 178473841, compoundHCID 178473853HCID 178473853, compound

Product 2

HCID 178473850HCID 178473850, compoundHCID 178473853HCID 178473853, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

{2-[3-(1-Acetyl-piperidin-4-yl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid was prepared from 1-[4-(trans-4-methyl-cyclohexylamino)-piperidin-1-yl]-ethanone and (2-amino-thiazol-5-ylsulfanyl)-acetic acid ethyl ester as described in general procedure (I). Amide coupling was then performed as follows using general procedure (J): {2-[3-(1-Acetyl-piperidin-4-yl)-3-(trans-4-methyl-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid is dissolved/suspended in 1 ml of DMF in a 4 ml glass vial equipped with a magnetic stirring bar and a screw cap. 0.015 g (0.088 mmol) of DHOBt+0.017 g (0.088 mmol) of EDAC is added, stirred for 1 h at room temperature (clear yellow mixture) after which 0.088 mmol of piperidine and 0.015 ml (0.088 mmol) of diisopropylethylamine is added. Stirred for 3 days at room temperature and purification by HPLC gave the title compound.

Workup

  1. customequipped with a magnetic stirring bar
  2. customa screw cap
  3. additionis added
  4. custompurification by HPLC

Sources & evidence

ORD record
ord-45dd9e86f8fe44aba86c0f47fcfbb14b
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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