Ammonium Chloride → HCID 46207858, compound

HRID 334338Notes

Reaction equation

HRID 334338 reaction equation
O[C@H]1CCCC[C@@H]1N1C(=O)C2C(=C3C=CC=CC3=CC=2)N=C1.[OH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[N:30]1[C:39](=[O:40])[C:38]2[C:33](=[C:34]3[CH:53]=[CH:52][CH:51]=[CH:50][C:35]3=[C:36]([CH2:41][C:42]3[CH:43]=[CH:44][C:45]([CH:48]=[O:49])=[N:46][CH:47]=3)[CH:37]=2)[N:32]=[CH:31]1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[N:30]1[C:39](=[O:40])[C:38]2[C:33](=[C:34]3[CH:53]=[CH:52][CH:51]=[CH:50][C:35]3=[C:36]([CH2:41][C:42]3[CH:43]=[CH:44][C:45]([CH:48]=[O:49])=[N:46][CH:47]=3)[CH:37]=2)[N:32]=[CH:31]1.[OH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[N:30]1[C:39](=[O:40])[C:38]2[C:33](=[C:34]3[CH:53]=[CH:52][CH:51]=[CH:50][C:35]3=[C:36]([CH2:41][C:42]3[CH:47]=[N:46][C:45]([CH2:48][OH:49])=[CH:44][CH:43]=3)[CH:37]=2)[N:32]=[CH:31]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 87383168HCID 87383168, compoundHCID 131732008HCID 131732008, compound

Product 2

HCID 46207858HCID 46207858, compoundHCID 87383168HCID 87383168, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Rac-5-({3-[trans-2-hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazolin-6-yl}methyl)pyridine-2-carbaldehyde was prepared by the same procedure as described for the synthesis of 6-[6-acetylpyridin-3-yl)methyl]-3-[(1S,2S)-2-hydroxycyclohexyl]benzo[h]quinazolin-4(3H)-one in Example 14. To a solution of rac-5-({3-[trans-2-hydroxycyclohexyl]-4-oxo-3,4-dihydrobenzo[h]quinazolin-6-yl}methyl)pyridine-2-carbaldehyde (0.070 g, 0.17 mmol) in 3 mL of MeOH was added sodium borohydride (0.0096 g, 0.25 mmol). After 1 h, the mixture was treated with saturated aqueous ammonium chloride, concentrated in vacuo, and diluted with ethyl acetate. The organic solution was washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 416.0 for [M+H]+: 1H NMR (400 MHz, CD3OD) δ 9.06-9.04 (m, 1H), 8.53 (s, 1H), 8.31 (s, 1H), 8.07 (s, 1H), 8.02-7.95 (m, 1H), 7.70-7.67 (m, 1H), 7.46-7.43 (m, 1H), 7.12-7.10 (m, 1H), 4.71 (s, 2H), 4.69-4.61 (m, 1H), 4.49 (s, 2H), 4.04-4.00 (m, 1H), 2.28-2.18 (m, 1H), 1.94-1.88 (m, 1H), 1.72-1.40 (m, 6H).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washThe organic solution was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-01984dfaf9944312afc6bcc60841f138
Source dataset
uspto-grants-2014_11
Patent number
US08883810B2

Reaction notes

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