Methylamine → HCID 67998436, compound

HRID 1425960Notes

Reaction equation

HRID 1425960 reaction equation
F[B-](F)(F)F.[N:6]1(OC(N(C)C)=[N+](C)C)[C:10]2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[Br:47][C:48]1[CH:49]=[CH:50][C:51]([C:54]2([C:57]([OH:59])=O)[CH2:56][CH2:55]2)=[N:52][CH:53]=1.C(N(C(C)C)C(C)C)C.CN>CN(C)C=O>[CH3:10][NH:6][C:57]([C:54]1([C:51]2[CH:50]=[CH:49][C:48]([Br:47])=[CH:53][N:52]=2)[CH2:56][CH2:55]1)=[O:59]

Participants

7

Reactant 5

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 694761531-(5-Bromopyridin-2-yl)cyclopropane-1-carboxylic acid

Product 1

HCID 67998436HCID 67998436, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (0.13 g; alternatively, 2-(7-aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate may be used) was added to a solution of 1-(5-bromo-pyridin-2-yl)-cyclopropanecarboxylic acid (0.10 g) and ethyl-diisopropyl-amine (70 μL) in N,N-dimethylformamide (1 mL) at room temperature. The solution was stirred for 20 min prior to the addition of methylamine (2 mol/L in tetrahydrofuran, 0.62 mL). The resulting solution was stirred at room temperature for 1 h and then concentrated. The residue was purified by HPLC on reversed phase (0.125% aqueous ammonia/methanol) to afford the title compound. Yield: 0.10 g (95% of theory); LC (method 1): tR=1.44 min; Mass spectrum (ESI+): m/z=255/257 (Br) [M+H]+.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 1 h
  2. concentrationconcentrated
  3. customThe residue was purified by HPLC on reversed phase (0.125% aqueous ammonia/methanol)

Sources & evidence

ORD record
ord-8db6d47ed5164dd8b0ac551ed82e784b
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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