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Hydrochloric Acid → HCID 86690314, compound

HRID 1521893
Notes
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Reaction equation

HRID 1521893 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

HCID 86690314HCID 86690314, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962
Water
Solvent

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-91e3ba976e524249a8c5fb6f1064d06c
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073932B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes