1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58788451, compound

HRID 1376162Notes

Reaction equation

HRID 1376162 reaction equation
C1C=CC2N(O)N=NC=2C=1.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]([OH:23])=O)=[CH:15]2.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.[NH2:44][CH:45]1[CH2:54][C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:47]([CH2:55][CH2:56][CH2:57][O:58][Si:59]([C:62]([CH3:65])([CH3:64])[CH3:63])([CH3:61])[CH3:60])[C:46]1=[O:66]>C(Cl)Cl>[Si:59]([O:58][CH2:57][CH2:56][CH2:55][N:47]1[C:48]2[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:54][CH:45]([NH:44][C:21]([C:16]2[NH:17][C:18]3[C:14]([CH:15]=2)=[CH:13][C:12]([Cl:11])=[CH:20][CH:19]=3)=[O:23])[C:46]1=[O:66])([C:62]([CH3:64])([CH3:65])[CH3:63])([CH3:61])[CH3:60]

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 58721822HCID 58721822, compound

Product 1

HCID 58788451HCID 58788451, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared exactly as in Method 7 using HOBT (174 mg, 1.3 mmol), 5-chloroindole-2-carboxylic acid (250 mg, 1.3 mmol), DIPEA (0.22 mL, 1.3 mmol), EDCI (308 mg, 1.6 mmol) and 3-amino-1-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-3,4-dihydroquinolin-2(1H)-one (Method 14, 432 mg, 1.3 mmol) in DCM (10 mL). This gave the title compound (548 mg, 82%) as a pale yellow solid.

Sources & evidence

ORD record
ord-e30be663573a46dda56820e07feb8e43
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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