1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22879946, compound

HRID 1535090Notes

Reaction equation

HRID 1535090 reaction equation
C1([C:7]([C@@H:29]([C@H]2OC(=O)[C@@H](C(C)C)C2)C)([C:11]2[N:15]3[CH:16]=[C:17]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)[N:18]=[C:19]([CH2:20][CH2:21][CH3:22])[C:14]3=[N:13][N:12]=2)[C:8](N)=[O:9])CCCCC1.[NH2:40][C@@H:41]([CH2:56][CH:57]1[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1)[C@@H:42]([OH:55])[CH2:43][C@@H:44]([CH:52]([CH3:54])[CH3:53])[C:45]([NH:47][CH2:48][CH2:49][CH2:50][CH3:51])=[O:46].[CH:63]1[CH:64]=[CH:65]C2N(O)N=[N:69][C:67]=2[CH:68]=1.CCN=C=NCCCN(C)C>O.CN(C=O)C>[CH2:48]([NH:47][C:45](=[O:46])[C@H:44]([CH:52]([CH3:53])[CH3:54])[CH2:43][C@H:42]([OH:55])[C@@H:41]([NH:40][C:8](=[O:9])[CH:7]([C:11]1[N:15]2[CH:16]=[C:17]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[N:18]=[C:19]([CH2:20][CH2:21][CH3:22])[C:14]2=[N:13][N:12]=1)[CH2:29][C:68]1[CH:67]=[N:69][CH:65]=[CH:64][CH:63]=1)[CH2:56][CH:57]1[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62]1)[CH2:49][CH2:50][CH3:51]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11151551HCID 11151551, compoundHCID 86745507HCID 86745507, compound

Product 1

HCID 22879946HCID 22879946, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of sodium 2-[8-propyl-6-(3-pyridyl)-1,2,4-triazolo[4,3-a]pyrazin-3-yl]-3-(3-pyridyl)propionate (A) (120 mg) in water (1 ml) was added to a solution of (2S,4S,5S)-5-amino-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropylhexanamide (98 mg) in DMF (9 ml). HOBT (40.5 mg) and EDAC (115 mg) were added and the solution was allowed 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 (7:93 v/v) to give (2S,4S,5S)-N-butyl-6-cyclohexyl-4-hydroxy-2-isopropyl-5-[(2RS)-2-(8-propyl-6-(3-pyridyl)-1,2,4-triazolo[4,3-a]pyrazin-3-yl)-3-(3-pyridyl)propionamido]hexanamide, as a foam (77 mg); NMR (d6 -DMSO/ D4 -acetic acid): 0.2-1.8 (complex m, 33H), 2.0 (m, 2H), 2.9-4.0 (complex m, 8 H), 4.9 (m, 1H), 7.4 (m, 1H), 7.5 (m, 1H), 7.9 (m, 1H), 8.5 (m, 2H), 8.7 (m, 2H), 9.3 (m, 2H); mass spectrum (+ve FAB, DMSO/m-nitrobenzyl alcohol): 697 (M+H)+, 624; microanalysis, found: C, 62.1; H, 7.9; N, 16.0%; C41H56N8O3. 2H2O requires: C, 67.2; H, 8.2; N, 15.3%.

Workup

  1. washeluting with methanol/dichloromethane (7:93 v/v)

Sources & evidence

ORD record
ord-d23df353d7de4a95905d218560509e41
Source dataset
uspto-grants-1992_02
Patent number
US05091425

Reaction notes

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