1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 9932099, compound

HRID 1375063Notes

Reaction equation

HRID 1375063 reaction equation
[C:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([Cl:13])=[CH:8][CH:7]=2)([OH:3])=O.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O.[NH2:40][C@H:41]([C:49]1[O:53][CH:52]=[N:51][C:50]=1[C:54]([O:56][CH3:57])=[O:55])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.C(OCC)(=O)C>[Cl:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4]([C:1]([NH:40][C@H:41]([C:49]1[O:53][CH:52]=[N:51][C:50]=1[C:54]([O:56][CH3:57])=[O:55])[CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:3])=[CH:12]2

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 86598628HCID 86598628, compound

Product 1

HCID 9932099HCID 9932099, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Carboxy-5-chloro-indole (146 mg, 0.75 mmol) was dissolved in DCM (5 ml) containing HOBT (126 mg, 0.93 mmol), DIPEA (290 mg, 2.25 mmol) and methyl (s)-5-(1-amino-2-phenylethyl)oxazole-4-carboxylate trifluoroacetate (Method 1; 360 mg, 0.75 mmol). EDAC (178 mg, 0.93 mmol) was added and the mixture stirred at ambient temperature for 4 hours. The reaction mixture was diluted with ethyl acetate (30 ml), washed with dilute citric acid, water and brine, dried over magnesium sulphate and concentrated. The crude material was purified by trituration with diethyl ether to give the title compound as a white solid. (227 mg, 65%)

Workup

  1. washwashed with dilute citric acid, water and brine
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated
  4. customThe crude material was purified by trituration with diethyl ether

Sources & evidence

ORD record
ord-1fb1f1cf61ee4bcd8f2da0f9d4f7c7f1
Source dataset
uspto-grants-2007_01
Patent number
US07166636B2

Reaction notes

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