Triethylamine → HCID 66864149, compound

HRID 2093066Notes

Reaction equation

HRID 2093066 reaction equation
C([CH:3]1[C:8]2[S:9][C:10]([C:12]([OH:14])=O)=[N:11][C:7]=2[CH2:6][CH2:5][N:4]1/[C:15](/[S:23][CH3:24])=[N:16]/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C.CCN=C=NCCCN(C)C.[CH:36]1[CH:37]=[CH:38][C:39]2[N:44](O)N=[N:42][C:40]=2[CH:41]=1.C(N(CC)CC)C>CN(C=O)C>[NH2:42][C:40]1[CH:41]=[CH:36][CH:37]=[CH:38][C:39]=1[NH:44][C:12]([C:10]1[S:9][C:8]2[CH2:3][N:4]([C:15]([S:23][CH3:24])=[N:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:5][CH2:6][C:7]=2[N:11]=1)=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178435272HCID 178435272, compound

Product 1

HCID 66864149HCID 66864149, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of ethyl 5-[(Z)-(methylthio)(phenylimino)methyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylic acid obtained in step III (1 eq), mono Boc-protected o-phenylene diamine (1.2 eq), EDCI (1.2 eq), HOBt (1.2 eq) and triethylamine in DMF were stirred at room temperature for 15 h. Solvent was evaporated and the residue was treated with etheral HCl at room temperature for 5-15 h. Solvent was evaporated and the residue was purified by either column chromatography or preparative HPLC to afford methyl 2-[(2-aminophenyl)carbamoyl]-N-phenyl-6,7-dihydro[1,3]thiazolo[5,4-c]pyridine-5(4H)carbimidothioate.

Workup

  1. customSolvent was evaporated
  2. additionthe residue was treated with etheral HCl at room temperature for 5-15 h
  3. customSolvent was evaporated
  4. customthe residue was purified by either column chromatography or preparative HPLC

Sources & evidence

ORD record
ord-5acb65ac66df4b9ea3fb5ce32c3877f8
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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