Hydrochloric Acid → HCID 178428336, compound

HRID 432776Notes

Reaction equation

C[O:2][C:3]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:22]=[C:21]([NH:23][C:24]3[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:8][C:7]=1[CH3:30])=[O:4].[OH-].[Na+].Cl>O.CCO>[C:3]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:22]=[C:21]([NH:23][C:24]3[NH:25][N:26]=[C:27]([CH3:29])[CH:28]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:8][C:7]=1[CH3:30])([OH:4])=[O:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of [2-(4-methoxycarbonylmethyl-3-methylphenylamino)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (IIc-64, 200 mg, 0.5 mmol) in a mixture of methanol/water (3/1, 8 mL) was treated with 1M NaOH (2 mL, 2 mmol). The mixture was heated at 70° C. for 2 hours and then neutralised with 1M HCl (2 mL, 2 mmol). The solid that formed was collected by filtration to afford the title compound (185 mg, 95%) as a pale yellow solid, mp 245° C. (dec.); 1H NMR (DMSO) δ 2.27 (6H, 2×s), 3.55 (2H, s), 6.49 (1H, s), 7.13 (1H, d), 7.26 (1H, t), 7.50 (1H, d), 7.62-7.78 (3H, m), 8.42 (1H, d), 9.34 (1H,d), 10.26 (1H, s), 12.36 (1H, s); IR (solid) 1660, 1590, 1562, 1504, 1427, 1385, 810, 776, 751, 693; MS 389.4 (M+H)+

Workup

customThe solid that formed
filtrationwas collected by filtration

Sources & evidence

ORD record: ord-494ed1d9665a48379ca76236d9ac36ad
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06664247B2

Reaction notes

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