Hydrochloric Acid → HCID 10388783, compound

HRID 1991081Notes

Reaction equation

HRID 1991081 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:18]=[CH:19]/[C:20]([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:24][C@H:23]2C)=[O:21])=[C:6]([NH:8]S(C2N=CN(C)C=2)(=O)=O)[CH:7]=1.[C:37](Cl)(=[O:41])[C:38](Cl)=O.CS(C)=O.C[CH2:48][N:49](CC)CC.C([O-])(=O)C.[NH4+].C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>C(Cl)Cl.O>[NH2:49][CH2:48][C@@H:23]1[CH2:24][N:25]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[CH2:26][CH2:27][N:22]1[C:20](=[O:21])/[CH:19]=[CH:18]/[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[NH:8][C:37](=[O:41])[CH3:38]

Participants

11

Reactant 8

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 10459706HCID 10459706, compound

Product 1

HCID 10388783HCID 10388783, compoundYield 5.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-50 °C

Procedure

Title compound of example 9 (0.5 g, 1.1 mmol) was dissolved in 5 ml DCM and was then slowly added at −70° C. to a mixture of 0.29 ml (2.8 mmol) oxalyl chloride, 0.39 ml (5.6 mmol) dimethyl sulfoxide and in 13 ml DCM. Stirring was continued at −70° C. for 3 hours, then the mixture was allowed to warm up to −50° C. and 1.5 ml (11.0 mmol) NEt3 and 20 ml water were added and the mixture was extracted with DCM. The organic layer was evaporated and immediately used for next step. The crude aldehyde was dissolved in 8 ml MeOH and 1.0 g (13.5 mmol) ammonium acetate and 62.8 mg (0.95 mmol) sodium cyanoborohydride were added. This mixture was stirred at room temperature over night, then 2 ml 1N HCl were added and stirring continued for 30 min. 2N NaOH was added to reach basic pH, and the mixture was extracted with DCM. The title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 90/10/1) and was isolated as a pale solid (25 mg, 5%)

Workup

  1. extractionthe mixture was extracted with DCM
  2. customThe organic layer was evaporated
  3. dissolutionThe crude aldehyde was dissolved in 8 ml MeOH
  4. stirringThis mixture was stirred at room temperature over night
  5. stirringstirring
  6. waitcontinued for 30 min
  7. extractionthe mixture was extracted with DCM
  8. customThe title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 90/10/1)

Sources & evidence

ORD record
ord-22f589e09fee4694b20eb9328ef7231a
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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