Hydrochloric Acid → 6-Chloro-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaen-16-one Hydrochloride

HRID 541818Notes

Reaction equation

HRID 541818 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18](Cl)[N:17]=2)[CH:10]=1)=[O:6].Cl>COCCO.O1CCOCC1>[ClH:22].[Cl:22][C:21]1[CH:20]=[N:19][C:18]2[NH:1][C:2]3[CH:26]=[CH:25][CH:24]=[C:4]([CH:3]=3)[C:5](=[O:6])[NH:7][CH2:8][C:9]3[CH:10]=[C:11]([NH:15][C:16]=1[N:17]=2)[CH:12]=[CH:13][CH:14]=3

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 579622043-Amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzamide

Product 1

HCID 668970696-Chloro-2,4,8,15,23-pentaazatetracyclo[15.3.1.1(3,7).1(9,13)]tricosa-1(21),3(23),4,6,9(22),10,12,17,19-nonaen-16-one HydrochlorideYield 62.5%

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 3-amino-N-{3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}benzamide (80.0 mg, 0.206 mmol) in 2-methoxyethanol (1.1 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (154 μL). The resulting mixture was heated at 150° C. in a microwave for 15 min. The cloudy mixture was filtered. The crude cake was recrystallized from MeOH to give the desired product as an off-white powder (25 mg, 34%). LCMS for C18H14ClN5O (M+H)+: m/z=352.0. 1H NMR (400 MHz, DMSO-d6): δ 10.06 (s, 1H), 9.50 (t, J=2.0 Hz, 1H), 9.05 (t, J=2.0 Hz, 1H), 8.24 (m, 1H), 7.86 (s, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.50 (t, J=8.0 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 7.28 (m, 2H), 7.10 (t, J=7.6 Hz, 1H), 6.96 (d, J=8.0 Hz, 1H), 4.42 (d, J=6.0 Hz, 2H).

Workup

  1. filtrationThe cloudy mixture was filtered
  2. customThe crude cake was recrystallized from MeOH

Sources & evidence

ORD record
ord-02ffddf7b17a4ce2861204eb9aae320e
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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