tert-butyl (2R)-2-[({7-(benzyloxy)-4-[3-chloro-4-fluoroanilino]quinazolin-5-yl}oxy)methyl]pyrrolidine-1-carboxylate → HCID 136344272, compound

HRID 1442998Notes

Reaction equation

C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)=[N:14][CH:15]=[N:16]2)=[C:11]([O:28][CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][N:31]2[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[F:26])[NH:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][C:11]=2[O:28][CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][N:31]2[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[N:16]=[CH:15][N:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of tert-butyl (2R)-2-[({7-(benzyloxy)-4-[3-chloro-4-fluoroanilino]-quinazolin-5-yl}oxy)methyl]pyrrolidine-1-carboxylate (230 mg) (obtained as described in Example 16) and 5% palladium on carbon in ethanol (5 ml) was stirred under hydrogen (5 bar pressure) at 25° C. for 16 hours. The mixture was then filtered and concentrated in vacuo to leave the tert-butyl (2R)-2-[({4-[3-chloro-4-fluoroanilino]-7-hydroxyquinazolin-5-yl}oxy)methyl]pyrrolidine-1-carboxylate as a light brown oil, which was used without further purification.

Workup

filtrationThe mixture was then filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e2eb935c87d247a4a909488938a299ad
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659279B2

Reaction notes

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