Diisopropylethylamine → Ammonium Acetate

HRID 2279229Notes

Reaction equation

HRID 2279229 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH3:25][C:26]1([CH3:34])[C:28]([CH3:30])([CH3:29])[CH:27]1[C:31]([OH:33])=[O:32].[CH2:35]([N:42]1[CH2:56][CH2:55][N:45]2[C:46]3[N:54]=[CH:53][CH:52]=[CH:51][C:47]=3[NH:48][CH2:49][CH2:50][CH:44]2[CH2:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:31]([O-:33])(=[O:32])[CH3:27].[NH4+:8].[CH2:35]([N:42]1[CH2:56][CH2:55][N:45]2[C:46]3[N:54]=[CH:53][CH:52]=[CH:51][C:47]=3[N:48]([C:31]([CH:27]3[C:28]([CH3:29])([CH3:30])[C:26]3([CH3:25])[CH3:34])=[O:33])[CH2:49][CH2:50][CH:44]2[CH2:43]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 54670219HCID 54670219, compound

Product 2

HCID 517165Ammonium AcetateHCID 54670314HCID 54670314, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (254 mg, 0.668 mmol) and 2,2,3,3-tetramethylcyclopropanecarboxylic acid (95 mg, 0.668 mmol) were added to a solution of the product of Example 52 (164 mg, 0.45 mmol) and diisopropylethylamine (0.16 mL, 0.89 mmol) in CH2Cl2 (5 mL). The mixture was stirred at room temperature for 45 hours, and then concentrated under vacuum. The residue was purified by preparative HPLC on a Phenomenex® Luna® C8(2) 5 μm 100 Å AXIA column (30×75 mm), eluting with methanol:10 mM ammonium acetate in water (10:90-95:5) to provide the title compound: 1H NMR (400 MHz, pyridine-d5, 110° C.) δ ppm 0.90 (s, 6H), 1.33 (s, 3H), 1.35 (s, 3H), 1.69 (q, J=6.1 Hz, 2H), 2.04 (s, 1H), 2.03-2.13 (m, 1H), 2.40 (td, J=10.8, 2.9 Hz, 1H), 2.64 (d, J=11.0 Hz, 1H), 2.78 (d, J=10.7 Hz, 1H), 3.33-3.44 (m, 1H), 3.43 (ddd, J=13.1, 11.0, 3.0 Hz, 1H), 3.49 (s, 2H), 3.57-3.72 (m, 2H), 4.03-4.13 (m, 1H), 6.80 (dd, J=7.5, 4.7 Hz, 1H), 7.22 (t, J=7.3 Hz, 1H), 7.27-7.33 (m, J=7.3, 7.3 Hz, 3H), 7.35-7.40 (m, 2H), 8.26 (dd, J=4.6, 1.8 Hz, 1H); MS (ESI) m/z 419 (M+H)+.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by preparative HPLC on a Phenomenex® Luna® C8(2) 5 μm 100 Å AXIA column (30×75 mm)
  3. washeluting with methanol

Sources & evidence

ORD record
ord-627428daca4d497397169c2a45f208fc
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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