Hydrochloric Acid → HCID 25006301, compound

HRID 1015416Notes

Reaction equation

C(N(CC)CC)C.[N:8]1([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[C:16]([NH2:25])=[N:17][C:18]([NH2:24])=[N:19]3)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Br[CH2:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=1.[ClH:38].O1CCOCC1>CN(C)C=O>[ClH:38].[CH:29]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:36]=[CH:37][C:28]=1[CH2:27][N:11]1[CH2:12][CH2:13][N:8]([C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[C:16]([NH2:25])=[N:17][C:18]([NH2:24])=[N:19]3)[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 60 °C

Procedure

In a 20 mL vial with stir bar, triethylamine (40 mg; 0.4 mmol) was added to a mixture of 5-piperazin-1-yl-quinazoline-2,4-diamine (50 mg; 0.2 mmol) and 2-(bromomethyl)naphthalene (59 mg; 0.26 mmol) in N,N-dimethylformamide and heated to 60° C. for 72 hours. Mixture was quenched with 1 mL of 1N NaOH and after 1.5 hours solids were collected by filtration and triturated with ethanol. Solids were stirred at room temperature with 4M HCl in Dioxane (2 eq). Solids were collected and dried to 60 mg of title compound. (71% yield). 1H NMR (500 MHz, DMSO-d6) δ 12.8 (s, 1H), 11.7 (s, 1H), 9.38 (s, 1H), 9.07 (s, 1H), 8.16 (s, 1H), 8.00 (m, 3H), 7.85 (dd, J=8.5, 1.0 Hz, 1H), 7.75 (t, J=8.0 Hz, 1H), 7.61 (m, 2H), 7.27 (d, J=8.5 Hz, 1H), 7.18 (d, J=8.5 Hz, 1H), 4.54 (s, 2H), 3.58 (m, 2H), 3.43 (d, J=11.5 Hz, 2H), 3.32 (t, J=12.0 Hz, 2H), 3.25 (d, J=12.0 Hz, 2H). ESIMS+385.8 m/z

Workup

customMixture was quenched with 1 mL of 1N NaOH and after 1.5 hours solids
filtrationwere collected by filtration
customtriturated with ethanol
customSolids were collected
dry with materialdried to 60 mg of title compound

Sources & evidence

ORD record: ord-ce99765ad9d34776b7b2e12b7fc90729
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985755B2

Reaction notes

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