Ammonium Chloride → HCID 178492246, compound

HRID 1876223Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:22])[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([C:20]#[N:21])[N:11]=2)=[CH:5][CH:4]=1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH3:22])[C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([C:20]3[NH:25][N:24]=[N:23][N:21]=3)[N:11]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To 4-[(4-methoxy-phenyl)-methyl-amino]-quinazoline-2-carbonitrile (100 mg, 0.34 mmol) in DMF (3.4 mL) was added sodium azide (269 mg, 4.1 mmol) and ammonium chloride (220 mg, 4.1 mmol). The reaction was heated to 130° C. for 15 min in a microwave. The reaction was quenched with aqueous NaHCO3 and diluted with EtOAc. The aqueous phase was acidified with HCl (12 M) to pH 1 and extracted with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated. Purification via gradient MPLC gave 15 mg (13%) of the title compound as a solid. 1H NMR (MeOH-d4) δ 7.91 (d, 1H), 7.74-7.70 (t, 1H), 7.30 (d, 2H), 7.16 (t, 1H), 7.06 (d, 2H), 7.0 (d, 1H), 3.86 (s, 3H), 3.82 (s, 3H); LC-MS (ESI+; 334 ([M+H]+)).

Workup

customThe reaction was quenched with aqueous NaHCO3
additiondiluted with EtOAc
extractionextracted with EtOAc
washThe combined organic phases were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customPurification via gradient MPLC

Sources & evidence

ORD record: ord-ebc8b57ccaa942dc83c394b54bc5b79a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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