Ammonium Chloride → HCID 86677082, compound

HRID 1520370Notes

Reaction equation

[F:1][CH:2]([F:30])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=3)[N:14]=[C:13]([C:24]3[CH:29]=[N:28][CH:27]=[CH:26][N:25]=3)[N:12]=2)[CH:7]=[CH:8][CH:9]=1.[NH4+].[Cl-]>CO.O.[Fe]>[F:30][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=3)[N:14]=[C:13]([C:24]3[CH:29]=[N:28][CH:27]=[CH:26][N:25]=3)[N:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of N-(3-(difluoromethoxy)phenyl)-6-nitro-2-(pyrazin-2-yl) quinazolin-4-amine (1.40 g, 3.4 mmol, 1.0 eq.) in MeOH-H2O (v/v, 3:1, 110 mL) was added NH4Cl (1.80 g, 34 mmol, 10.0 eq.) and Fe (1.91 g, 34 mmol, 10.0 eq.). The resulting mixture was stirred at 60° C. for 3 h. After the reaction was completed, the mixture was cooled to room temperature, and the iron was filtered off. The filtrate was concentrated to 15 ml, and a precipitate formed and was collected and dried in vacuo to give 1.13 g of N4-(3-(difluoromethoxy)phenyl)-2-(pyrazin-2-yl)quinazoline-4,6-diamine as a pale yellow solid (87.5%). LCMS m/z=381.1 (M+1) (Method B) (retention time=1.60 min), 1H-NMR (400 MHz, DMSO-d6): δ 9.69 (s, 1H), 9.52 (d, J=1.2 Hz, 1H), 8.75 (d, J=2.4 Hz, 1H), 8.69 (d, J=2.4 Hz, 1H), 8.30 (s, 1H), 7.87 (dd, J=8.4, 0.8 Hz, 1H), 7.72 (d, J=8.8 Hz, 1H), 7.49-7.42 (m, 2H), 7.33-7.32 (m, 1H), 7.31 (t, J=7.4 Hz, 1H), 5.85 (s, 2H).

Workup

temperaturethe mixture was cooled to room temperature
filtrationthe iron was filtered off
concentrationThe filtrate was concentrated to 15 ml
customa precipitate formed
customwas collected
customdried in vacuo

Sources & evidence

ORD record: ord-8be2ef3972144f088e5f0a9bf0a762e6
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073890B2

Reaction notes

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