D-Psicose → HCID 117779006, compound

HRID 2206563Notes

Reaction equation

HRID 2206563 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[CH2:11][NH:12][C:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH:24]([C:26]2[CH:27]=[C:28]([CH:33]=[CH:34][CH:35]=2)[C:29]([O:31]C)=O)[CH3:25])[C:16]=1[CH3:36])=[O:14].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O.C(O)C.[CH3:52][NH2:53]>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[CH2:11][NH:12][C:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH:24]([C:26]2[CH:35]=[CH:34][CH:33]=[C:28]([C:29](=[O:31])[NH:53][CH3:52])[CH:27]=2)[CH3:25])[C:16]=1[CH3:36])=[O:14]

Participants

4

Reactant 3

HCID 441036D-PsicoseHCID 22028356Methylamine ethanolHCID 117778697HCID 117778697, compound

Product 1

HCID 117779006HCID 117779006, compoundYield 30%

Procedure

Methyl 3-(1-(3-(((4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methy)carbamoyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-1-yl)ethyl)benzoate (20 mg, 0.041 mmol) was added to 30% methylamine ethanol solution (10 mL). The mixture was stirred under 50 Psi at 100° C. for 12 hours in a 100 mL of sealed tube. The solvent was evaporated and the residue was purified by preparative-HPLC (Instrument: Gilson GX281 Column: ASB C18 150*25 mm*5 um Mobile phase A: water with 0.05% ammonia solution Mobile phase B: MeCN Column temperature: 30° C. Gradient: 17-47% B 15 min) to afford the title compound (17.4 mg, yield: 30%). LRMS (M+H+) m/z: calcd 488.22. found 488.0. 1H NMR (400 MHz, chloroform-d) δ ppm 2.01 (d. J=7.28 Hz, 3H) 2.26 (s, 3H) 2.50 (s, 3H) 2.96 (d, J=4.63 Hz, 3H) 3.91 (s, 3H) 4.64 (d, J=5.51 Hz, 2H) 5.95 (s, 1H) 6.14 (br. S., 1H) 6.55 (d, J=8.16 Hz, 1H) 7.05-7.13 (m, 1H) 7.33 (t, J=8.05 Hz, 1H) 7.51-7.59 (m, 1H) 7.60-7.64 (m, 1H) 8.24 (d, J=5.51 Hz, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative-HPLC (Instrument: Gilson GX281 Column: ASB C18 150*25 mm*5 um Mobile phase A: water with 0.05% ammonia solution Mobile phase B: MeCN Column temperature: 30° C. Gradient: 17-47% B 15 min)

Sources & evidence

ORD record
ord-41691e6a7f204247afa1dbfacd2eb9e7
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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