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

HRID 1929370Notes

Reaction equation

HRID 1929370 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). 1H NMR (CD3OD, 400 MHz) δ 2.25-2.32 (2H, s), 3.40-3.45 (2H, m), 3.55-3.60 (2H, m), 3.90-3.95 (2H, m), 4.07-4.12 (2H, m), 7.14-7.17 (1H, t), 7.81-7.89 (2H, m), 8.10-8.12 (1H, d), 8.17 (1H, s), 8.22-8.24 (1H, d), 8.29-8.31 (1H, d), 8.98-9.00 (1H, d); MS (ES+) 348.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-b87b606f5c8e4d5ab75f4fa57833b56c
Source dataset
uspto-grants-2012_05
Patent number
US08188071B2

Reaction notes

Loading…