Dimethylamine → HCID 51000867, compound

HRID 1774911Notes

Reaction equation

HRID 1774911 reaction equation
[OH:1][C@@H:2]1[C@@H:7]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]4[CH:32]=[CH:31][CH:30]=[CH:29][C:13]4=[C:14]([CH2:19][C:20]4[CH:21]=[CH:22][C:23]([C:26]([OH:28])=O)=[N:24][CH:25]=4)[CH:15]=3)[N:10]=[CH:9]2)[CH2:6][CH2:5][O:4][CH2:3]1.[CH3:33][NH:34][CH3:35].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O.ClCCl>[OH:1][C@@H:2]1[C@@H:7]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[C:12]4[CH:32]=[CH:31][CH:30]=[CH:29][C:13]4=[C:14]([CH2:19][C:20]4[CH:21]=[CH:22][C:23]([C:26]([N:34]([CH3:35])[CH3:33])=[O:28])=[N:24][CH:25]=4)[CH:15]=3)[N:10]=[CH:9]2)[CH2:6][CH2:5][O:4][CH2:3]1

Participants

8

Reactant 4

HCID 674Dimethylamine2×HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 699351085-({3-[(3R,4S)-3-Hydroxytetrahydro-2H-pyran-4-yl]-4-oxo-3,4-dihydrobenzo[h]quinazolin-6-yl}methyl)pyridine-2-carboxylic acid

Product 1

HCID 51000867HCID 51000867, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-({3-[(3R,4S)-3-Hydroxytetrahydro-2H-pyran-4-yl]4-oxo-3,4-dihydrobenzo[h]quinazolin-6-yl}methyl)pyridine-2-carboxylic acid (Example 18, 0.030 g, 0.070 mmol) in 1 mL of DMF was added dimethylamine (0.087 mL, 0.17 mmol), triethylamine (0.019 mL, 0.14 mmol), and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (0.046 g, 0.10 mmol). After 1 h, additional dimethylamine (0.17 mL, 0.35 mmol) was added. After 2 h, the mixture was diluted with water and dichloromethane, and the organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-5% methanol in dichloromethane to provide the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 459.2039 for [M+H]+ [Calc'd for C26H27N4O4, [M+H]+=459.2027]: 1H NMR (400 MHz, CDCl3) δ 8.89-8.87 (m, 1H), 8.41 (s, 1H), 8.28 (s, 1H), 7.76 (s, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.63-7.54 (m, 2H), 7.41 (s, 2H), 4.82-4.75 (m, 1H), 4.34 (br s, 1H), 4.27 (s, 2H), 4.23-4.18 (m, 2H), 4.03 (s, 1H), 3.58-3.51 (m, 1H), 3.34-3.28 (m, 1H), 3.09 (s, 3H), 2.99 (s, 3H), 2.23-2.12 (m, 1H), 2.00-1.91 (m, 1H).

Workup

  1. waitAfter 2 h
  2. dry with materialthe organic solution was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-7ecd7bba33ea4a9aa168170aae937095
Source dataset
uspto-grants-2016_02
Patent number
US09260418B2

Reaction notes

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