Hydrochloric Acid → HCID 57524507, compound

HRID 882022Notes

Reaction equation

HRID 882022 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[N:21]=[C:20]4[N:22]([CH3:36])[C:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][C:24]=5[C:19]4=[CH:18][CH:17]=3)[C:12](=[O:37])[CH:11]=2)=[N:6][CH:7]=1.Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[N:21]=[C:20]4[N:22]([CH3:36])[C:23]5[CH2:28][CH2:27][NH:26][CH2:25][C:24]=5[C:19]4=[CH:18][CH:17]=3)[C:12](=[O:37])[CH:11]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67988825HCID 67988825, compound

Product 1

HCID 57524507HCID 57524507, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 2-(4-((5-fluoropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (0.14 g, 0.28 mmol) was treated with 1.25 M HCl in MeOH (7.0 mL), and the resulting suspension was stirred at ambient temperature for 18 h. The resulting solids were collected by filtration, dissolved in CH2Cl2 (30 mL), and washed with saturated NaHCO3 solution (50 mL). The resulting layers were separated, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure to dryness. Flash chromatography (12 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 4 column volumes, increased to 0:100 over 20 column volumes and held for 34 column volumes) provided the title compound (75 mg, 67%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.62 (d, J=2.7 Hz, 1H), 7.92-7.78 (m, 3H), 7.69-7.62 (m, 1H), 7.23 (d, J=8.1 Hz, 1H), 6.18 (dd, J=7.8, 2.7 Hz, 1H), 5.98 (d, J=2.7 Hz, 1H), 5.23 (s, 2H), 3.87 (s, 2H), 3.65 (s, 3H), 3.08 (t, J=5.7 Hz, 2H), 2.75 (t, J=5.4 Hz, 2H).

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. dissolutiondissolved in CH2Cl2 (30 mL)
  3. washwashed with saturated NaHCO3 solution (50 mL)
  4. customThe resulting layers were separated
  5. dry with materialthe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure to dryness
  7. temperatureFlash chromatography (12 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 4 column volumes, increased to 0:100 over 20 column volumes and held for 34 column volumes)

Sources & evidence

ORD record
ord-31ea0972d5004065987ab4bd623706d9
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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