1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57270838, compound

HRID 1535091Notes

Reaction equation

HRID 1535091 reaction equation
[CH2:1]([C:4]1[C:5]2[N:6]([C:16]([CH2:19][C:20]([O-:22])=O)=[N:17][N:18]=2)[CH:7]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:9]=1)[CH2:2][CH3:3].[Na+].[CH:24]1([C:30]([C@@H:52]([C@H:54]2[O:58][C:57](=[O:59])[C@@H:56]([CH:60](C)C)[CH2:55]2)C)(C2N3C=C(C4C=NC=CC=4)N=C(CCC)C3=NN=2)C(N)=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C1C=CC2N(O)N=[N:69][C:67]=2C=1.CC[N:75]=C=NCCCN(C)C>O.CN(C=O)C>[CH:24]1([CH2:30][C@H:52]([NH:75][C:20](=[O:22])[CH2:19][C:16]2[N:6]3[CH:7]=[C:8]([C:10]4[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=4)[N:9]=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]3=[N:18][N:17]=2)[C@@H:54]([OH:58])[CH2:55][C@@H:56]([CH3:60])[C:57]([NH:69][CH3:67])=[O:59])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 23709823HCID 23709823, compoundHCID 86745507HCID 86745507, compound

Product 1

HCID 57270838HCID 57270838, 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 (81 mg) in water (1 ml) was added to a solution of (2R,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-N,2-dimethylhexanamide (A) (55 mg) in DMF (9 ml). HOBT (33.7 mg) and EDAC (96 mg) were added and the solution was left to stand overnight. The reaction mixture was worked up by a similar procedure to that described in Example 1, followed by flash chromatography eluting with methanol/dichloromethane (1:9 v/v) to give (2R,4S,5S)-6-cyclohexyl-4-hydroxy-N,2-dimethyl-5-[8-propyl-6-(3-pyridyl)-1,2,4-triazolo[4,3-a]pyrazin-3-yl]acetamidohexanamide, as a foam (27 mg); NMR (400 MHz, d6 -DMSO/d4 -acetic acid): 0.7-1.7 (complex m, 21H), 2.0 (m, 2H), 2.5 (m, 1H), 2.55 (s, 3H), 3.3 (t, 2H), 3.4 (m, 1H), 3.8 (m, 1H), 4.3 (m, partially exchanged with d4 -acetic acid), 7.6 (dd, 1H), 8.5 (m, 1H), 8.7 (dd, 1H), 9.0 (s, 1H), 9.3 (dd, 1H); mass spectrum (+ve FAB, DMSO/glycerol): 536 (M+H)+, 505, 297, 280; microanalysis, found: C, 62.3; H, 7.4, N, 17.6%; C29H41N7O3.H2O requires : C, 62.9, H, 7.8; N, 17.7%.

Workup

  1. waitthe solution was left
  2. washeluting with methanol/dichloromethane (1:9 v/v)

Sources & evidence

ORD record
ord-e76ffa0293ca4eea884b7006b52d2969
Source dataset
uspto-grants-1992_02
Patent number
US05091425

Reaction notes

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