HCID 137227863, compound → HCID 136366851, compound

HRID 2062226Notes

Reaction equation

[OH:1][C:2]([C:4]([F:7])([F:6])[F:5])=[O:3].C([O:15][CH2:16][C@H:17]1[CH2:22][N:21]([C:23]2[C:32]3[C:27](=[CH:28][C:29]([CH3:33])=[CH:30][CH:31]=3)[N:26]=[C:25]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[OH:40])[N:24]=2)[CH2:20][CH2:19][N:18]1[C:41]([O:43][C@@H:44]1[CH2:48][CH2:47][O:46][CH2:45]1)=[O:42])C1C=CC=CC=1>C(O)C.[OH-].[OH-].[Pd+2]>[F:5][C:4]([F:7])([F:6])[C:2]([OH:3])=[O:1].[OH:15][CH2:16][C@H:17]1[CH2:22][N:21]([C:23]2[C:32]3[C:27](=[CH:28][C:29]([CH3:33])=[CH:30][CH:31]=3)[N:26]=[C:25]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[OH:40])[N:24]=2)[CH2:20][CH2:19][N:18]1[C:41]([O:43][C@@H:44]1[CH2:48][CH2:47][O:46][CH2:45]1)=[O:42]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (2R)-(R)-tetrahydrofuran-3-yl 2-((benzyloxy)methyl)-4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate TFA salt (94 mg, 0.17 mmol) in ethanol was added Pd(OH)2 (78 mg), and the reaction was heated at 50° C. under an H2 atmosphere at ambient pressure. The reaction was filtered, and purification using reverse phase HPLC (10-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)) gave (2R)-(R)-tetrahydrofuran-3-yl 2-(hydroxymethyl)-4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazine-1-carboxylate trifluoroacetate. LC/MS: m/z 465.5 (M+H)+ at 2.23 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

filtrationThe reaction was filtered
custompurification

Sources & evidence

ORD record: ord-402e463ec8374ddb8331f4a3c6526923
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283354B2

Reaction notes

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