1,2-Dichloroethane → HCID 86656601, compound

HRID 2036897Notes

Reaction equation

HRID 2036897 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH2:17][NH:16][CH2:15][CH2:14]2)=[O:10].[CH3:21][C:22]1[N:23]([CH2:27][CH2:28]C)[CH:24]=[CH:25][N:26]=1.C1C=CC2N([OH:39])N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[CH3:21][C:22]1[N:23]([CH2:27][C:28]([N:16]2[CH2:15][CH2:14][C:13]3[C:18](=[CH:19][CH:20]=[C:11]([C:9]([NH:8][O:7][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)=[O:10])[CH:12]=3)[CH2:17]2)=[O:39])[CH:24]=[CH:25][N:26]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 529336HCID 529336, compoundHCID 86656618HCID 86656618, compound

Product 1

HCID 86656601HCID 86656601, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 200 mg N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide, 61 mg 3-(2-methyl-1H-imidazol-1-yl)propan acid, 111 mg HOBt, 276 mg EDC, 0.603 ml triethylamine and 7 ml DMF is stirred overnight. The reaction mixture is quenched with 3 ml water and 5 ml dichloromethane. The organic phase is separated, the water phase extracted with dichloromethane. The combined organic phases are dried and evaporated. 315 ml of yellow oil is obtained, which is further purified by preparative HPLC-methods.

Workup

  1. customThe reaction mixture is quenched with 3 ml water and 5 ml dichloromethane
  2. customThe organic phase is separated
  3. extractionthe water phase extracted with dichloromethane
  4. customThe combined organic phases are dried
  5. customevaporated

Sources & evidence

ORD record
ord-d039a2960ff74659a5a16d1a0b5c8b87
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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