Acetic Acid → Tert-butyl [4-(3-hydroxy-3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-2-yl)pyridin-3-yl]carbamate

HRID 1043484Notes

Reaction equation

HRID 1043484 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[CH:18]=[N:17][CH:16]=[CH:15][C:9]=3/[C:10](=[N:13]/[OH:14])/[C:11](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:19]([O:23][C:24](=[O:34])[NH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][C:31]=1[CH:32]=O)([CH3:22])([CH3:21])[CH3:20].C([O-])(=O)C.[NH4+:39].C(O)(=O)C>C(OCC)(=O)C.O>[OH:14][N:13]1[C:10]2[C:9]3[CH:15]=[CH:16][N:17]=[CH:18][C:8]=3[NH:7][C:6]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:11]=2[N:39]=[C:32]1[C:31]1[CH:30]=[CH:29][N:28]=[CH:27][C:26]=1[NH:25][C:24](=[O:34])[O:23][C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 14177126Tert-butyl 4-formylpyridin-3-ylcarbamateHCID 178516816HCID 178516816, compound

Product 1

HCID 16071783Tert-butyl [4-(3-hydroxy-3,8-dihydroimidazo[4,5-d]dipyrido[2,3-b:4',3'-f]azepin-2-yl)pyridin-3-yl]carbamateYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (6Z)-5H-dipyrido[2,3-b:4′,3′-f]azepine-5,6(11H)-dione 6-oxime (80.0 mg, 0.333 mmol), tert-butyl-(4-formylpyridin-3-yl)carbamate, ammonium acetate (0.513 g, 6.66 mmol), water (0.12 mL) and acetic acid (0.76 mL) was stirred at 80° C. for 3 h. The solution was diluted with ethyl acetate and water, the organic solution was washed with brine, dried over MgSO4 and concentrated. The crude residue was purified by preparative LCMS to yield the desired product (102 mg, 69%). LCMS for C23H22N2O3(M+H)+: m/z=444.2.

Workup

  1. washthe organic solution was washed with brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was purified by preparative LCMS

Sources & evidence

ORD record
ord-166f182f99d2494ca2d4e28802eaaf36
Source dataset
uspto-grants-2013_10
Patent number
US08563541B2

Reaction notes

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