1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 14787983, compound

HRID 1535089Notes

Reaction equation

HRID 1535089 reaction equation
[CH2:1]([C:5]1[C:6]2[N:7]([C:17]([CH:20](CC3C=NC=CC=3)[C:21]([O-:23])=O)=[N:18][N:19]=2)[CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=C[CH:12]=2)[N:10]=1)[CH:2]([CH3:4])C.[Na+].[NH2:32][C@@H:33]([CH2:48][CH:49]1[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]1)[C@@H:34]([OH:47])[CH2:35][C@@H:36]([CH:44]([CH3:46])[CH3:45])[C:37]([NH:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:38].C1C=CC2N(O)N=[N:61]C=2C=1.CCN=C=NCCCN(C)C>O.CN(C=O)C>[CH2:40]([NH:39][C:37](=[O:38])[C@H:36]([CH:44]([CH3:45])[CH3:46])[CH2:35][C@H:34]([OH:47])[C@@H:33]([NH:32][C:21](=[O:23])[CH2:20][C:17]1[N:7]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:61][CH:14]=[CH:15][CH:16]=3)[N:10]=[C:5]([CH2:1][CH2:2][CH3:4])[C:6]2=[N:19][N:18]=1)[CH2:48][CH:49]1[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]1)[CH2:41][CH2:42][CH3:43]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 11151551HCID 11151551, compoundHCID 23679985HCID 23679985, compound

Product 1

HCID 14787983HCID 14787983, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of sodium 8-propyl-6-(3-pyridyl)-1,2,4-triazolo[4,3-a]pyrazin-3-ylacetate (A) (112 mg) in water (1.5 ml) was added to a solution of (2S,4S,5S)-5-amino-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropylhexanamide (114 mg) in DMF (13.5 ml). HOBT (47 mg) and EDAC (67 mg) were added, and the solution was allowed to stand overnight. A further quantity of EDAC (67 mg) was added and the solution was again allowed to stand overnight. The reaction mixture was worked up using a similar procedure to that described in Example 1, and purified by flash chromatography eluting with methanol/ dichloromethane (6:94 v/v) to give (2S,4S,5S)-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropyl-5-[8-propyl-6-(3-pyridyl)-1,2,4-triazolo[4,3-a]pyrazin-3-yl]acetamidohexanamide, as a foam (60 mg); NMR (d6 -DMSO/d4 -acetic acid): 0.8-1.8 (complex m, 32H), 2.1 (m, 3H), 2.8-3.5 (m, 5H0, 3.8 (m, 1H), 4.4 (m, partially exchanged with d4 -acetic acid), 7.7 (dd, 1H), 8.6 (m, 1H), 8.7 (d, 1H), 8.9 (s, 1H), 9.3 (s, 1H); mass spectrum (+ve FAB, methanol/glycerol: 606 (M+H)+, 533, 327, 297, 290; microanalysis, found: C, 6.34; H, 8.1; N, 14.8%; C34H51N7O3,2H2O requires C, 63.7; H, 8.6; N, 15.3%.

Workup

  1. waitto stand overnight
  2. custompurified by flash chromatography
  3. washeluting with methanol/ dichloromethane (6:94 v/v)

Sources & evidence

ORD record
ord-7d0441ad036d4443a67cd01cd4d3c692
Source dataset
uspto-grants-1992_02
Patent number
US05091425

Reaction notes

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