Hydrochloric Acid → HCID 86690314, compound

HRID 1428663Notes

Reaction equation

HRID 1428663 reaction equation
[CH:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:10]=2)[N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:4]=1)=[O:2].N#N.[BH4-].[Na+].Cl>CCO.O>[OH:2][CH2:1][C:3]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[N:10]=2)[N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 4311764Sodium borohydrideHCID 71657495HCID 71657495, compound

Product 1

HCID 86690314HCID 86690314, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7-(7-Formyl-2,3-di-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoic acid (Example 2.1) (42 mg, 0.092 mmol) in EtOH (1 ml) was degassed with N2 and treated with sodium borohydride (5.23 mg, 0.138 mmol). After stirring at RT for 16 hours, the mixture was added to water (30 ml) and the pH was adjusted to pH 1 using 2M HCl. The aqueous portion was extracted with DCM (×3) and the combined extracts were concentrated under reduced pressure. The crude product was triturated with EtOAc/iso-hexane to afford the titled compound as an orange solid;

Workup

  1. extractionThe aqueous portion was extracted with DCM (×3)
  2. concentrationthe combined extracts were concentrated under reduced pressure
  3. customThe crude product was triturated with EtOAc/iso-hexane

Sources & evidence

ORD record
ord-fd688016fbc347b6a3c461921d74bdef
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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