Diisopropylethylamine → HCID 58091617, compound

HRID 1874002Notes

Reaction equation

HRID 1874002 reaction equation
C([N:4]([CH2:8]C)[CH:5]([CH3:7])[CH3:6])(C)C.[B:10]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)([OH:12])[OH:11].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(O)(=O)C(O)=O.CNC1CC1>CC#N>[CH:5]1([N:4]([CH3:8])[C:17]([C:16]2[CH:15]=[CH:14][C:13]([B:10]([OH:11])[OH:12])=[CH:21][CH:20]=2)=[O:19])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3121834-Carboxyphenylboronic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12612353HCID 12612353, compound

Product 1

HCID 58091617HCID 58091617, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Diisopropylethylamine (1.693 mL, 9.69 mmol) was added to a suspension of 4-boronobenzoic acid (321.7 mg, 1.939 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (806.4 mg, 2.121 mmol) in CH3CN (20 mL). After 50 min at room temperature, N-methylcyclopropanamine oxalic acid salt (315.8 mg, 1.960 mmol) was added. After 1.25 h at room temperature, the mixture was purified by reverse phase HPLC (Sunfire S10 30×250 mm column, 30-50% solvent B gradient) to give the expected product (303.6 mg, 72% yield). MS (ES+) m/z: 220 (M+H); LC retention time: 2.40 min (analytical HPLC Method A).

Workup

  1. waitAfter 1.25 h at room temperature
  2. customthe mixture was purified by reverse phase HPLC (Sunfire S10 30×250 mm column, 30-50% solvent B gradient)

Sources & evidence

ORD record
ord-53947bbb8da347ac92b7c79c2c3ca7bc
Source dataset
uspto-grants-2012_11
Patent number
US08304539B2

Reaction notes

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