Hydrochloric Acid → (1-(1,4-Diazepan-1-yl)isoquinolin-3-yl)(2-aminopyridin-3-yl)methanone dihydrochloride

HRID 401481Notes

Reaction equation

HRID 401481 reaction equation
[NH2:1][C:2]1[N:33]=[CH:32][CH:31]=[CH:30][C:3]=1[C:4]([C:6]1[N:7]=[C:8]([N:16]2[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]2)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5].[ClH:34]>O1CCOCC1>[ClH:34].[ClH:34].[N:16]1([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:6]([C:4]([C:3]3[C:2]([NH2:1])=[N:33][CH:32]=[CH:31][CH:30]=3)=[O:5])[N:7]=2)[CH2:22][CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57690466Tert-butyl 4-(3-(2-aminonicotinoyl)isoquinolin-1-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 67048264(1-(1,4-Diazepan-1-yl)isoquinolin-3-yl)(2-aminopyridin-3-yl)methanone dihydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a suspension of tert-butyl 4-(3-(2-aminonicotinoyl)isoquinolin-1-yl)-1,4-diazepane-1-carboxylate (18 mg, 0.04 mmol) in 1,4-dioxane (1 ml) was added 4 M HCl in 1,4-dioxane (0.5 ml). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated to dryness to leave title compound as a solid (16.6 mg, 98% yield).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-8073752b17e44fd78c6bde11cdaa25f8
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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