1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 23121803, compound

HRID 2113217Notes

Reaction equation

HRID 2113217 reaction equation
C(N(C(C)C)CC)(C)C.CN(C)CCCN=C=NCC.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25].[CH2:27]([O:34][C:35]1[CH:36]=[C:37]([CH:50]=[C:51]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:52]=1)[C:38]([NH:40][C:41]1[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[CH:43][N:42]=1)=[O:39])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[CH2:54]([O:53][C:51]1[CH:50]=[C:37]([CH:36]=[C:35]([O:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:52]=1)[C:38]([NH:40][C:41]1[CH:49]=[CH:48][C:44]([C:45]([NH:25][CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])=[O:46])=[CH:43][N:42]=1)=[O:39])[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 101613156-[[3,5-bis(phenylmethoxy)benzoyl]amino]pyridine-3-carboxylic acid

Product 1

HCID 23121803HCID 23121803, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (DIPEA, 0.23 ml, 1.3 mM) then 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide (EDC, 126 mg, 0.66 mM) were added to a solution of 2-dimethylaminoethylamine (0.57 ml, 0.53 mM) and 6-{[3,5-Di-(benzyloxy)benzoyl]amino}nicotinic acid (0.20 g, 0.44 mM) in dichloromethane (10 ml) under argon at ambient temperature. After 16 hours the reaction mixture was evaporated in vacuo and then chromatographed on SiO2 using a gradient elution of 10 to 25% methanol in dichloromethane. The fractions containing product were evaporated to give a cream solid (0.052 g, 25%); 1H NMR δ (d6-DMSO): 2.67 (6H, s); 3.11 (2H, m); 3.62 (2H, m); 5.18 (4H, s); 6.88 (1H, s); 7.27-7.52 (12H, br m); 8.18-8.36 (2H, m); 8.90 (1H, s); 10.20 (1H, br s).

Workup

  1. customAfter 16 hours the reaction mixture was evaporated in vacuo
  2. customchromatographed on SiO2 using
  3. washa gradient elution of 10 to 25% methanol in dichloromethane
  4. additionThe fractions containing product
  5. customwere evaporated

Sources & evidence

ORD record
ord-8407744444a7439f89dcf4e15fdfeff2
Source dataset
uspto-grants-2009_04
Patent number
US07524957B2

Reaction notes

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