Sodium borohydride → HCID 54763442, compound

HRID 2365266Notes

Reaction equation

HRID 2365266 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[N:15]1[CH:27]([CH2:28][CH:29]=[O:30])[C:26]2[C:17](=[CH:18][C:19]([CH2:31][C:32]3[CH:33]=[N:34][C:35]([Cl:38])=[CH:36][CH:37]=3)=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[C:16]1=[O:39])(C(C)(C)C)(C)C.[BH4-].[Na+]>ClCCl.CO.Cl.C(=O)(O)[O-].[Na+]>[Cl:38][C:35]1[N:34]=[CH:33][C:32]([CH2:31][C:19]2[CH:18]=[C:17]3[C:16](=[O:39])[N:15]([C@H:10]4[CH2:11][CH2:12][CH2:13][CH2:14][C@@H:9]4[OH:8])[CH:27]([CH2:28][CH2:29][OH:30])[C:26]3=[C:25]3[C:20]=2[CH:21]=[CH:22][CH:23]=[N:24]3)=[CH:37][CH:36]=1

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 86682413HCID 86682413, compound

Product 1

HCID 54763442HCID 54763442, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of {8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-5-[(6-chloropyridin-3-yl)methyl]-7-oxo-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-9-yl}acetaldehyde (see Example 22, 0.030 g, 0.053 mmol) in a mixture of 0.4 mL of dichloromethane and 0.1 mL of methanol at 0° C. was added sodium borohydride (2.0 mg, 0.053 mmol). The mixture was allowed to warm to ambient temperature and after 15 hr, hydrochloric acid (3 N aqueous, 5 drops) was added. After 24 hr, the mixture was diluted with saturated aqueous sodium bicarbonate and extracted 3× with ethyl acetate. The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative reverse phase HPLC to provide the titled compound that gave a mass ion (ES+) of 452.1735 for [M+H]+ [calc'd for C25H27ClN3O3, [M+H]+=452.1735]: 1H NMR (400 MHz, CD3OD) δ 9.00-8.98 (m, 1H), 8.62-8.59 (m, 1H), 8.31-8.30 (m, 1H), 7.69 (s, 1H), 7.65-7.62 (m, 2H), 7.37 (d, J=8.3 Hz, 1H), 5.44-5.41 (m, 2H), 4.60 (s, 2H), 4.42-4.36 (m, 1H), 3.76-3.66 (m, 1H), 3.15-3.01 (m, 2H), 2.58-2.51 (m, 1H), 2.16-2.13 (m, 1H), 1.97-1.93 (m, 2H), 1.82-1.79 (m, 2H), 1.46-1.40 (m, 3H) ppm.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via preparative reverse phase HPLC

Sources & evidence

ORD record
ord-185c71e54c86440aab38e937736824ba
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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