Phosphorus oxychloride → HCID 66992789, compound

HRID 717835Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:25]([O:27][CH3:28])=[O:26])[C:5]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)=[N:6][C:7]=1[CH2:8][NH:9][CH:10]=O.P(Cl)(Cl)(Cl)=O>>[ClH:1].[Cl:1][C:2]1[C:7]2[N:6]([CH:10]=[N:9][CH:8]=2)[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[C:4]([C:25]([O:27][CH3:28])=[O:26])[CH:3]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 58515969HCID 58515969, compound

Product 1

HCID 66992789HCID 66992789, compoundYield 192.1%

Procedure

A solution of tert-butyl 4-{5-chloro-6-[(formylamino)methyl]-3-(methoxycarbonyl)pyridin-2-yl}piperazine-1-carboxylate (670 mg, 2.2 mmol) in phosphoryl chloride (5.0 mL, 54 mmol) was heated to 70° C. for 30 minutes. Evaporation gave the desired compound (700 mg, 98%). LCMS calculated for C13H16ClN4O2 (M+H)+: m/z=295.1. found: 294.9.

Workup

customEvaporation

Sources & evidence

ORD record: ord-31c8a2b8d0df4c8595dd4211f13e1a49
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193721B2

Reaction notes

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