1,2-Dichloroethane → HCID 59548746, compound

HRID 1810986Notes

Reaction equation

HRID 1810986 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([OH:22])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:37][N:38]1[CH2:43][CH2:42][C:41]2[N:44]=[C:45]([NH2:47])[S:46][C:40]=2[CH2:39]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20](=[O:22])[NH:47][C:45]2[S:46][C:40]3[CH2:39][N:38]([CH3:37])[CH2:43][CH2:42][C:41]=3[N:44]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 23979985-methyl-4H,5H,6H,7H-[1,3]thiazolo[5,4-c]pyridin-2-amineHCID 27567762-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

Product 1

HCID 59548746HCID 59548746, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Dissolved 4-(2-carboxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.30 g, 0.98 mmol), EDC (0.23 g, 1.20 mmol) and HOBT (0.18 g, 1.20 mmol) into 1 mL of DMF. The mixture stirred for 1 h. To this is added 5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylamine (0.16 g, 0.98 mmol) and N,N-diisopropylethylamine (0.37 mL, 2.00 mmol). The mixture is placed under a stream of Ar and heated at 50° C. for 16 h. The mixture is then diluted with 50 mL CH2Cl2, quenched with 20 mL of saturated NH4Cl; washed with 2×20 mL of H2O, and washed with 1×20 mL of brine. The resultant organic phase was dried with MgSO4, filtered and concentrated to provide 0.38 g, 85% yield of 4-[2-(5-methyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. customquenched with 20 mL of saturated NH4Cl
  2. washwashed with 2×20 mL of H2O
  3. washwashed with 1×20 mL of brine
  4. dry with materialThe resultant organic phase was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-450bf91f57f248ad84c22706020db5ed
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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