Sodium cyanoborohydride → HCID 69935535, compound

HRID 341097Notes

Reaction equation

HRID 341097 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[C:5]([N:9]2[C:33](=[O:34])[C:12]3=[CH:13][N:14]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([N:28]5[CH:32]=[CH:31][CH:30]=[N:29]5)=[CH:24][CH:23]=4)[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[C:11]3=[N:10]2)[N:4]=[CH:3]1.C([BH3-])#N.[Na+]>O1CCCC1.ClCCl>[OH:8][CH2:7][C:6]1[N:2]([CH3:1])[CH:3]=[N:4][C:5]=1[N:9]1[C:33](=[O:34])[C:12]2=[CH:13][N:14]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[CH:31][CH:30]=[N:29]4)=[CH:24][CH:23]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]2=[N:10]1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 86668683HCID 86668683, compound

Product 1

HCID 69935535HCID 69935535, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-Methyl-4-(3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)-1H-imidazole-5-carbaldehyde (Example 555, 50 mg, 0.11 mmol) was dissolved in tetrahydrofuran (2 mL) and dichloromethane (15 mL), cooled to 0° C. and treated with sodium cyanoborohydride (0.033 mL, 1 M tetrahydrofuran solution, 0.033 mmol, 0.3 equiv). After stirring for 5 minutes at 0° C., the mixture was warmed to ambient temperature and stirred for 1 hour. Additional sodium cyanoborohydride (0.033 mL, 1 M tetrahydrofuran solution, 0.033 mmol, 0.3 equiv) was added and after 1 hour, the mixture was concentrated in vacuo. The residue was purified by preparative reverse phase HPLC (85:15 to 40:60; water containing 0.5% trifluoroacetic acid:acetonitrile containing 0.5% trifluoroacetic acid). The appropriate fractions were concentrated in vacuo, providing the titled compound: 1H-NMR (400 MHz, d6-DMSO) δ 9.04 (1H, br s), 8.37 (1H, br d, J=4.7 Hz), 8.20 (1H, m), 7.85 (1H, d, J=8.8 Hz), 7.77 (2H, d, J=8.3 Hz), 7.74-7.65 (4H, m), 7.61 (1H, br t, J=6.7 Hz), 7.44 (2H, d, J=7.6 Hz), 6.51 (1H, m), 5.82 (2H, s), 4.00 (2H, s) 2.65 (3H, s) ppm; high resolution mass spectrometry (ES+) m/z 452.1842 [(M+H)+; calculated for C25H22N7O2: 452.1829].

Workup

  1. temperaturethe mixture was warmed to ambient temperature
  2. stirringstirred for 1 hour
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe residue was purified by preparative reverse phase HPLC (85:15 to 40:60; water containing 0.5% trifluoroacetic acid:acetonitrile containing 0.5% trifluoroacetic acid)
  5. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-74b610c6d2644915879c1bcefca52f2b
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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