1-Hydroxybenzotriazole → Racemic (2'S,3S,4'R)-6-chloro-4'-[5-chloro-2-(1-hydroxycarbamoyl-1-methyl-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione
Reaction equation
ClC1C=C2N[C:9](=[O:39])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27]([OH:29])=O)([CH3:26])[CH3:25])[CH2:14][C:13](=[O:30])[NH:12][CH:11]3[C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[CH3:38])C2=CC=1.CCN=C=NCCCN(C)C.[ClH:51].[CH:52]1[CH:53]=[CH:54][C:55]2N(O)N=[N:58][C:56]=2[CH:57]=1.CCN(C(C)C)C(C)C.Cl.[NH2:72][OH:73]>C1COCC1>[Cl:51][C:52]1[CH:57]=[C:56]2[NH:58][C:9](=[O:39])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[O:23][C:24]([C:27](=[O:29])[NH:72][OH:73])([CH3:25])[CH3:26])[CH2:14][C:13](=[O:30])[NH:12][CH:11]3[C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=3[CH3:38])[C:55]2=[CH:54][CH:53]=1Participants
7
Reactant 5
HCID 757711-Hydroxybenzotriazole
HCID 81531Diisopropylethylamine
HCID 443297Hydroxyamine hydrochloride
HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
HCID 765680156-chloro-4'-[5-chloro-2-(1-hydroxycarbonyl-1-methyl-ethoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl) spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dioneProduct 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-hydroxycarbonyl-1-methyl-ethoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (30 mg, 0.053 mmol) prepared in Example 1f, EDCl (20 mg, 0.1 mmol), HOBt (16 mg, 0.1 mmol) and DIPEA (40 mg, 0.3 mmol) in THF (1 mL) was added hydroxylamine hydrochloride ((18 mg, 0.26 mmol). The mixture was stirred at room temperature overnight and purified by prep-HPLC to give the title compound as a white solid (14 mg).
Workup
- custompurified by prep-HPLC
Sources & evidence
- ORD record
- ord-d77589e63d8a4c8aa8ee818c9645a23e
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776875B2
Reaction notes
Loading…