Hydrochloric Acid → N-{3-Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-7-[(2E)-4-(dimethylamino)but-2-enoyl]-5,6,7,8-tetrahydropyrido[4',3':4,5]furo[2,3-d]pyrimidin-4-amine

HRID 38624Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH2:27][CH2:28][N:29]([C:31](OC(C)(C)C)=[O:32])[CH2:30][C:25]=4[O:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl.O1CCOCC1.Cl.[CH3:46][N:47]([CH3:54])[CH2:48]/[CH:49]=[CH:50]/C(O)=O>CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH2:27][CH2:28][N:29]([C:31](=[O:32])/[CH:50]=[CH:49]/[CH2:48][N:47]([CH3:54])[CH3:46])[CH2:30][C:25]=4[O:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5,8-dihydropyrido[4′,3′:4,5]furo-[2,3-d]pyrimidine-7(6H)-carboxylate from Example 86A (18 mg, 0.034 mmol) was dissolved in 2-propanol (1.0 mL) and treated with 4 M gaseous hydrogen chloride in dioxane (0.25 mL, 1.0 mmol). The mixture was heated to 80° C. for 2 h. Subsequently, the solvent was removed in vacuo. The residue was reacted in analogy to Example 89 with (2E)-4-(dimethylamino)but-2-enoic acid hydrochloride from Example 1A (8.0 mg, 0.048 mmol) to yield 7.0 mg (38%) of the title compound.

Workup

customSubsequently, the solvent was removed in vacuo

Sources & evidence

ORD record: ord-d2e5717d50054717a825f758352221d4
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524722B2

Reaction notes

Loading…