Sodium Hydroxide → 3-(2'-amino-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzamide

HRID 2096623Notes

Reaction equation

C([NH:5][C:6]1[S:7][CH2:8][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]#[N:24])[CH:18]=3)[O:13][CH:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:11]2)[N:10]=1)(C)(C)C.[OH-:34].[Na+]>Cl>[NH2:5][C:6]1[S:7][CH2:8][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=4)[C:23]([NH2:24])=[O:34])[CH:18]=3)[O:13][CH:12]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:11]2)[N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(2′-(tert-butylamino)-2-phenyl-5′H-spiro[chroman-4,4′-thiazole]-6-yl)benzonitrile (30 mg, 0.066 mmol) in concentrated HCl (5 mL) was stirred at 100° C. for 2 h. Aqueous NaOH (6 N) was added until pH=8. The mixture was extracted with EtOAc and the organic layer was dried and concentrated to give the residue, which was purified by preparative TLC to give 3-(2′-amino-2-phenyl-5′H-spiro[chroman-4,4′-thiazole]-6-yl)benzamide (20 mg, 73%).

Workup

extractionThe mixture was extracted with EtOAc
customthe organic layer was dried
concentrationconcentrated
customto give the residue, which
customwas purified by preparative TLC

Sources & evidence

ORD record: ord-84a0c8e2e7fb4e18a5692c058198071a
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450308B2

Reaction notes

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