Ethanaminium, N,N,N-triethyl-, fluoride (1:1) → HCID 178484173, compound

HRID 1254382Notes

Reaction equation

HRID 1254382 reaction equation
[C:1]([N:3]=[C:4]([N:26]1[CH2:31][CH2:30][CH2:29][C@@H:28]([C@:32]([OH:45])([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH2:27]1)[NH:5][C@@H:6]([CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:7][N:8](C)[C:9](OCC[Si](C)(C)C)=O)#[N:2].[N+](CC)(CC)(CC)CC.[F-]>CC#N>[C:1]([N:3]=[C:4]([N:26]1[CH2:31][CH2:30][CH2:29][C@@H:28]([C@:32]([OH:45])([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH2:27]1)[NH:5][C@@H:6]([CH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1)[CH2:7][NH:8][CH3:9])#[N:2]

Participants

4

Reactant 2

HCID 69582Ethanaminium, N,N,N-triethyl-, fluoride (1:1)HCID 178494981HCID 178494981, compound

Product 1

HCID 178484173HCID 178484173, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (3R)—N′-cyano-N-((S)-3-cyclohexyl-1-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carboxamidine (145 mg, 0.21 mmol) and Et4NF (160 mg, 1.1 mmol) in MeCN (5 mL) was heated at 100° C. in the microwave for 7 min. The reaction mixture was directly submitted to prep HPLC to afford (3R)—N′-cyano-N-((S)-3-cyclohexyl-1-(methylamino)propan-2-yl)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carboxamidine (16 mg, 14%).

Sources & evidence

ORD record
ord-c3e9147e7a5d4836b81c1ee5fd062105
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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