Acetonitrile → HCID 178507513, compound

HRID 46140Notes

Reaction equation

HRID 46140 reaction equation
NC1C=CC=CC=1[N:8]1[C:12](=[O:13])[CH:11]([CH2:14][C:15]([OH:17])=O)[S:10][CH:9]1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)[CH2:28][CH2:29][CH2:30][N:31]=C=NCC.[CH3:37][C:38]#N.C(Cl)Cl.C[N:44]([CH:46]=O)C>>[NH2:31][C:30]1[CH:29]=[CH:28][CH:38]=[CH:37][C:46]=1[NH:44][C:15](=[O:17])[CH2:14][CH:11]1[S:10][C:9]([NH:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:8][C:12]1=[O:13]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22350042dichloromethane N,N-dimethylformamideHCID 86606010HCID 86606010, compound

Product 1

HCID 178507513HCID 178507513, compound

Conditions

Temperature
40 °C

Procedure

N-(2-Aminophenyl)-2-(2-anilino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)acetic acid, prepared using method 2 above, (30 mg, 1 eq) was dissolved in a mixture of DCM/DMF (2 mL/2 mL) and O-phenylendiamine (15 mg, 1.1 eq), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC, 30 mg, 1.3 eq) were then added sequentially. The reaction mixture was stirred 40° C. for 2 h.Separated between DCM and H2O, the organic layer concentrated to give a crude orange brown oil used directly in the next step: HPLC 43%, RT=0.93 min (System B, 2-95% MeCN over 2 min); MS [M+H]+ m/z=341.

Workup

  1. additionwere then added sequentially
  2. customSeparated between DCM and H2O
  3. concentrationthe organic layer concentrated
  4. customto give a crude orange brown oil

Sources & evidence

ORD record
ord-af7b1420cac94b7fa1e6753fc66a451b
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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