Triethylamine → HCID 86664068, compound

HRID 712370Notes

Reaction equation

HRID 712370 reaction equation
Cl[C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:10]3[S:14][C:13]([NH:15][C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:12][C:11]=3[CH:21]=2)[S:4][N:3]=1.C(N(CC)CC)C.Cl.[CH2:36]([C:38]1([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)C>CN(C=O)C>[CH2:19]([NH:18][C:16]([NH:15][C:13]1[S:14][C:10]2[C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[CH:8][C:7]([C:5]3[S:4][N:3]=[C:2]([N:41]4[CH2:42][CH2:43][C:38]([CH3:36])([C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:39][CH2:40]4)[N:6]=3)=[CH:21][C:11]=2[N:12]=1)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53393421Ethyl 4-ethyl-4-piperidinecarboxylate hydrochlorideHCID 866640671-[5-(3-Chloro-1,2,4-thiadiazol-5-yl)-7-(pyridin-2-yl)-1,3-benzothiazol-2-yl]-3-ethylurea

Product 1

HCID 86664068HCID 86664068, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[5-(3-chloro-1,2,4-thiadiazol-5-yl)-7-(pyridin-2-yl)-1,3-benzothiazol-2-yl]-3-ethylurea (100 mg, 0.24 mmol) and Triethylamine (73 mg, 0.72 mmol) in DMF (10 mL) was added ethyl 4-ethylpiperidine-4-carboxylate hydrochloride (100 mg, 0.48 mmol) and the mixture stirred at rt for 1 h giving a suspension. LCMS showed only SM so the reaction was heated at 90° C. for 3 days after which time LCMS showed a major product peak. The reaction mixture was concentrated in vacuo to give an orange gum, which was purified by flash column chromatography (Biotage SP4, 12 g 2-10% MeOH/DCM)) to give the desired product as a cream solid (100 mg, 52%) MS: 552.11 [M+H]+.

Workup

  1. customgiving a suspension
  2. temperaturewas heated at 90° C. for 3 days after which time LCMS
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give an orange gum, which
  5. customwas purified by flash column chromatography (Biotage SP4, 12 g 2-10% MeOH/DCM))

Sources & evidence

ORD record
ord-237c9bb300df4a39ba9d1569cd611941
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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