Hydrochloric Acid → HCID 118274497, compound

HRID 522221Notes

Reaction equation

HRID 522221 reaction equation
[F:1][C:2]1[CH:30]=[C:6]2[CH:7]=[CH:8][C:9]3=[N:10][NH:11][C:12]4[C:13](=[CH:14][N:15]([CH3:29])[CH2:16][C:17]=4[C:18]4[CH2:19][CH2:20][N:21]([CH2:25][C:26](O)=[O:27])[CH2:22][CH2:23][CH:24]=4)[C:4](=[C:5]23)[CH:3]=1.[NH:31]1[CH2:34][CH:33]([OH:35])[CH2:32]1.Cl.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C)C=O>[F:1][C:2]1[CH:30]=[C:6]2[CH:7]=[CH:8][C:9]3=[N:10][NH:11][C:12]4[C:13](=[CH:14][N:15]([CH3:29])[CH2:16][C:17]=4[C:18]4[CH2:19][CH2:20][N:21]([CH2:25][C:26]([N:31]5[CH2:34][CH:33]([OH:35])[CH2:32]5)=[O:27])[CH2:22][CH2:23][CH:24]=4)[C:4](=[C:5]23)[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 15142903-HydroxyazetidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118274123HCID 118274123, compound

Product 1

HCID 118274497HCID 118274497, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 90B (60 mg, 0.125 mmol), azetidin-3-ol, hydrochloric acid (20.57 mg, 0.188 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate (V) (57.1 mg, 0.150 mmol) and triethylamine (87 μL, 0.626 mmol) in 2 mL N,N-dimethylformamide was stirred at room temperature overnight. The mixture was extracted with dichloromethane and purified by flash chromatography on silica using an Analogix system (0-10% methanol/dichloromethane) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 2.46-2.90 (m, 10H), 3.17 (d, J=5.1 Hz, 2H), 3.62 (dd, J=10.3, 4.4 Hz, 1H), 3.89-4.14 (m, 5H), 4.33-4.61 (m, 2H), 5.72 (d, J=5.9 Hz, 1H), 5.92 (t, J=6.3 Hz, 1H), 7.18-7.35 (m, 3H), 7.69 (dd, J=10.4, 3.0 Hz, 1H), 8.22 (d, J=5.2 Hz, 1H), 11.51 (s, 1H). MS (ESI+) m/z 462 (M+H)+.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. custompurified by flash chromatography on silica using an Analogix system (0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7380b864c928437eaeb32aee28f7fc58
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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