Hydrochloric Acid → HCID 73055947, compound

HRID 2284405Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=1)[N:8]=[C:7]([C:22]1[CH:23]=[N:24][C:25]([NH:28]C(=O)OC(C)(C)C)=[N:26][CH:27]=1)[N:6]=[C:5]2[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.Cl>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:13]=1)[N:8]=[C:7]([C:22]1[CH:23]=[N:24][C:25]([NH2:28])=[N:26][CH:27]=1)[N:6]=[C:5]2[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 25 mL flask, tert-butyl (5-(6-fluoro-7-(3-(methylsulfonyl)phenyl)-4-morpholinoquinazolin-2-yl)pyrimidin-2-yl)carbamate (0.06 g, 0.0001 mol) and 1,4-dioxane (4 mL) were added. The reaction mixture was cooled to 0° C. To the flask, 4 N HCl in 1,4-dioxane (6 mL) was added. The reaction mixture was stirred at room temperature for 12 hours. The volatiles were evaporated under reduced pressure to provide the crude product. The crude product was purified by preparative HPLC (10 mM ammonium acetate in water and acetonitrile) to provide the title compound (0.01 g, 7%). 1H NMR (400 MHz, DMSO-d6): δ 9.21 (s, 2H), 8.23 (s, 1H), 8.13-8.07 (m, 3H), 8.02 (d, J=11.2 Hz, 1H), 7.88 (t, J=8.0 Hz, 1H), 7.42 (br s, 2H), 3.96 (br s, 4H), 3.84 (br s, 4H), 3.43 (s, 3H): LC-MS (ESI): Calculated mass: 480.1; Observed mass [M+H]+: 481.1 (RT=0.30 min).

Workup

customThe volatiles were evaporated under reduced pressure
customto provide the crude product
customThe crude product was purified by preparative HPLC (10 mM ammonium acetate in water and acetonitrile)

Sources & evidence

ORD record: ord-80f052415ffe45f78b7da83db2134b69
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145411B2

Reaction notes

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