Hydrogen Bromide → HCID 66864394, compound

HRID 1615845Notes

Reaction equation

N[C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][C@@:7]3([CH2:17]2)[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]3=[O:16])=[CH:4][C:3]=1[C:20]#[N:21].N([O-])=O.[Na+].[NH4+].[OH-].[BrH:28]>O.[Cu]Br>[Br:28][C:2]1[CH:19]=[C:18]2[C:5]([CH2:6][C@@:7]3([CH2:17]2)[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]3=[O:16])=[CH:4][C:3]=1[C:20]#[N:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of (2R)-6-amino-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridine]-5-carbonitrile (200 mg, 0.72 mmol) in 25% HBr at 0° C. was added a solution of sodium nitrite (61.4 mg, 0.89 mmol) in H2O (0.3 mL) dropwise. The cooled mixture was then added to a cooled solution of copper(I)bromide (107 mg, 0.746 mmol) in 48% HBr (0.557 mL, 4.92 mmol). The reaction mixture was stirred at 0° C. for 1 h then warmed to ambient temperature. H2O (5 mL) was added and the mixture was made basic by addition of concentrated NH4OH. The resulting precipitate was collected by filtration and washed with H2O to provide the title compound in sufficient purity for the next step. MS: m/z=341 (M+1).

Workup

temperaturethen warmed to ambient temperature
filtrationThe resulting precipitate was collected by filtration
washwashed with H2O

Sources & evidence

ORD record: ord-99266c55f18641d293f06daf83fa1284
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765759B2

Reaction notes

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