Triethylamine → HCID 46866218, compound

HRID 1187747Notes

Reaction equation

HRID 1187747 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[CH:17]=[CH:16][C:12]=2[C:13](O)=[O:14])[CH3:9])=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.[N:34]1(OC(N(C)C)=[N+](C)C)[C:38]2C=CC=CC=2N=N1.C(N(CC)CC)C.CN.O1CCCC1>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[CH:17]=[CH:16][C:12]=2[C:13]([NH:34][CH3:38])=[O:14])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66615946Methylamine tetrahydrofuranHCID 67007881HCID 67007881, compound

Product 1

HCID 46866218HCID 46866218, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

80 mg of (S)-2-[1-(4-Fluorophenyl)ethylamino]-6-(pyrazin-2-ylamino) nicotinic acid was dissolved in 1 ml of tetrahydrofuran, 86 mg of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate salt (HBTU) and 59 mg of triethylamine were added thereto. The mixture was stirred at room temperature for 30 minutes, and then 119 μl of 2M methylamine/tetrahydrofuran solution was added thereto, and the mixture was stirred for 5 hours. The reaction solution was purified by silica gel column chromatography to obtain 45 mg of the objective compound as white powder.

Workup

  1. stirringthe mixture was stirred for 5 hours
  2. customThe reaction solution was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-84a95610645d460d9e25919155b75178
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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