Hydrochloric Acid → HCID 58515984, compound

HRID 717845Notes

Reaction equation

HRID 717845 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Cl:26])[C:7]2[N:8]([CH:23]=[N:24][CH:25]=2)[C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16](OC(C)(C)C)=O)[CH2:12][CH2:11]1)(=[O:3])[CH3:2].Cl.[C:28]1(=O)[CH2:31]C[CH2:29]1.C([BH3-])#N.[Na+]>O1CCOCC1.C(#N)C.O1CCCC1>[Cl:26][C:6]1[C:7]2[N:8]([CH:23]=[N:24][CH:25]=2)[C:9]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]3[CH2:31][CH2:28][CH2:29]3)[CH2:12][CH2:11]2)=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14496CyclobutanoneHCID 5003444Sodium cyanoborohydrideHCID 58515955HCID 58515955, compound

Product 1

HCID 58515984HCID 58515984, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-(6-acetyl-8-chloroimidazo[1,5-a]pyridine-5-yl)piperazine-1-carboxylate (33 mg, 0.087 mmol) was treated with a solution of 4 M hydrogen chloride in 1,4-dioxane (1.0 mL) and evaporated to dryness. Cyclobutanone (13 μL, 0.18 mmol), tetrahydrofuran (0.5 mL) and acetonitrile (0.5 mL) were added and the mixture was stirred for 30 minutes. Sodium cyanoborohydride (17 mg, 0.26 mmol) was added and was stirred for 4 hours. Purification by preparative LCMS (pH 10) gave the desired compound (18 mg, 61%). LCMS calculated for C17H22ClN4O (M+H)+: m/z=333.1. found: 332.9.

Workup

  1. customevaporated to dryness
  2. stirringwas stirred for 4 hours
  3. customPurification by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-03116ec03e86427dbeb3b2e58fc0e4ba
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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