Hydrochloric Acid → HCID 71657496, compound

HRID 1428664Notes

Reaction equation

HRID 1428664 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]([O:34][CH2:35][CH3:36])=[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]([O:34][CH2:35][CH3:36])=[O:33])[CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 4311764Sodium borohydrideHCID 86690313HCID 86690313, compound2×

Product 1

HCID 71657496HCID 71657496, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 7-(7-Formyl-2,3-di-p-tolyl-5H-pyrrolo[2,3-b]pyrazin-5-yl)heptanoate (Intermediate C) (47 mg, 0.097 mmol) in EtOH (2 ml) was degassed with N2 treated with sodium borohydride (5.52 mg, 0.146 mmol) was added. After stirring at RT for 3 hours, the mixture was diluted with 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. Purification of the crude product by chromatography on silica eluting with 0-40% EtOAc in iso-hexane afforded the titled compound as an orange oil;

Workup

  1. additionwas added
  2. extractionThe aqueous portion was extracted with DCM (×3)
  3. concentrationthe combined extracts were concentrated under reduced pressure
  4. customPurification of the crude product by chromatography on silica eluting with 0-40% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-9bbcf79e2898454ea42aac3a9dfa9560
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

Loading…