Triethylamine → HCID 86669644, compound

HRID 1623892Notes

Reaction equation

HRID 1623892 reaction equation
[C:1]([N:5]1[C:12]2[C@@H:11]3[CH2:13][C@@H:10]3[CH2:9][C:8]=2[C:7]([C:14](O)=[O:15])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[C:48]1([C:54]([NH2:57])([CH3:56])[CH3:55])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[CH3:55][C:54]([NH:57][C:14]([C:7]1[C:8]2[CH2:9][C@H:10]3[CH2:13][C@H:11]3[C:12]=2[N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[N:6]=1)=[O:15])([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH3:56]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 68509CumylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68182343HCID 68182343, compound

Product 1

HCID 86669644HCID 86669644, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1aR,5aR)-2-tert-butyl-1a,2,5,5a-tetrahydro-1H-2,3-diazacyclopropa[a]pentalene-4-carboxylic acid (30 mg, 0.136 mmol), HATU (55 mg, 0.143 mmol) in DMF (1 mL) was added Et3N (16 mg, 0.15 mmol). After stirring for 5 min at room temperature, 2-phenylpropan-2-amine (20 mg, 0.143 mmol) was added into the reaction. The reaction was stirred for 1 h at room temperature, and purified by preparative HPLC to give the title compound (25 mg). LCMS m/z=338.5 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 0.34 (td, J=4.5 and 3.4 Hz, 1H), 1.11 (td, J=7.8 and 4.5 Hz, 1H), 1.63 (s, 9H), 1.78 (s, 6H), 2.11-2.18 (m, 2H), 2.75 (d, J=16.7 Hz, 1H), 2.86 (dd, J=16.6 and 5.8 Hz, 1H), 7.21 (t, J=7.3 Hz, 1H), 7.32 (t, J=8.0 Hz, 2H), 7.36 (bs, 1H), 7.42-7.46 (m, 2H).

Workup

  1. stirringThe reaction was stirred for 1 h at room temperature
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-00238358c5954cb58a08ef10d0b637e9
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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