1,2-Dichloroethane → HCID 66787107, compound

HRID 1025747Notes

Reaction equation

HRID 1025747 reaction equation
[OH:1][C:2]1([C:12]2[S:13][CH:14]=[C:15]([C:17]([OH:19])=O)[N:16]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1.CN.C[CH2:23][N:24](CC)CC.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.CCOC(C)=O>[OH:1][C:2]1([C:12]2[S:13][CH:14]=[C:15]([C:17]([NH:24][CH3:23])=[O:19])[N:16]=2)[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH2:4][CH2:3]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6329MethylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 66786970HCID 66786970, compound

Product 1

HCID 66787107HCID 66787107, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(8-hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)-1,3-thiazole-4-carboxylic acid (0.30 g, 1.05 mmol) and methylamine (2M in THF, 2 mL, 4 mmol) in CH2Cl2 (10 mL) was added Et3N (0.5 mL, 3.6 mmol) followed by EDC (0.242 g, 1.262 mmol) and HOBt (0.193 g, 1.26 mmol). The mixture was stirred at room temperature overnight. Then the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3 and brine. The organic layer was dried (MgSO4), concentrated and flash chromatographed (50% EtOAc EtOAc) to give 0.16 g of the title compound in 50% yield. MS (EI) calcd: (M+H)+=299.1; found: 299.0.

Workup

  1. washwashed with saturated Na2CO3 and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customflash chromatographed (50% EtOAc EtOAc)

Sources & evidence

ORD record
ord-10e29c876fb446d899f932af897f9d9f
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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