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Ethanol → HCID 178419985, compound

HRID 931262
Notes
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Reaction equation

HRID 931262 reaction equation
[N:1]1[N:2]=[C:3]([CH:9]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]3[N:20]=[C:19]([NH2:21])[C:18]([N+:22]([O-])=O)=[CH:17][CH:16]=3)[CH2:10]2)[N:4]2[CH2:8][CH2:7][CH2:6][C:5]=12.[CH:25]1([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]=O)[N:29]=2)[CH2:27][CH2:26]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(O)C>O>[CH:25]1([C:28]2[N:29]=[C:30]([C:34]3[NH:21][C:19]4=[N:20][C:15]([N:11]5[CH2:12][CH2:13][CH2:14][CH:9]([C:3]6[N:4]7[CH2:8][CH2:7][CH2:6][C:5]7=[N:1][N:2]=6)[CH2:10]5)=[CH:16][CH:17]=[C:18]4[N:22]=3)[CH:31]=[CH:32][CH:33]=2)[CH2:27][CH2:26]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 24489Sodium DithioniteHCID 193617216-CyclopropylpicolinaldehydeHCID 898542026-(3-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amine2×

Product 1

HCID 178419985HCID 178419985, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 6-(3-(6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-3-yl)piperidin-1-yl)-3-nitropyridin-2-amine (Intermediate 45) (300 mg, 0.91 mmol), 2-cyclopropylpyridine-6-aldehyde (187.5 mg, 1.27 mmol), sodium dithionite (602.6 mg, 4.46 mmol), ethanol (15 mL) and water (2.4 mL) in a sealed tube was heated to 110° C. for 16 h. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was and purified via preparative TLC to afford the title compound (80 mg, 21%) as a racemic mixture. MS (ES+) (M+H) 427.3; LCMS retention time 2.687 min (Method J). 1H NMR (400 MHz, CDCl3) δ 1.02-1.15 (m, 4H), 1.73-1.82 (m, 1H), 1.89-2.13 (m, 3H), 2.21 (d, 1H), 2.74-2.85 (m, 2H), 2.94-3.01 (m, 2H), 3.02-3.12 (m, 2H), 3.21-3.32 (m, 1H), 3.91-4.10 (m, 2H), 4.33 (d, 1H), 4.65 (d, 1H), 6.75 (d, 1H), 7.20 (d, 1H), 7.66 (t, 2H), 7.88 (d, 1H), 8.05 (d, 1H), 10.20 (br s, 1H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified via preparative TLC

Sources & evidence

ORD record
ord-5da4bbb99d2a4e2abc4a98809079b05e
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296745B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes