Cyanogen Bromide → HCID 86718420, compound

HRID 1911780Notes

Reaction equation

[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:10]=[C:11]2[N:26]=[C:25]([CH3:27])[N:24]([CH3:28])[C:12]2=[N:13][C:14]=1[N:15]([CH2:20][CH:21]1[CH2:23][CH2:22]1)[CH2:16][CH:17]1[CH2:19][CH2:18]1.C(=O)(O)[O-].[Na+].[N:43]#[C:44]Br>CO>[CH:17]1([CH2:16][N:15]([CH2:20][CH:21]2[CH2:23][CH2:22]2)[C:14]2[N:13]=[C:12]3[N:24]([CH3:28])[C:25]([CH3:27])=[N:26][C:11]3=[CH:10][C:9]=2[CH2:8][N:7]([CH2:6][C:5]2[CH:29]=[C:30]([C:32]([F:33])([F:35])[F:34])[CH:31]=[C:3]([C:2]([F:36])([F:1])[F:37])[CH:4]=2)[C:44]#[N:43])[CH2:18][CH2:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of {6-[(3,5-bis-trifluoromethyl-benzylamino)-methyl]-2,3-dimethyl-3H-imidazo[4,5-b]pyridin-5-yl}-bis-cyclopropylmethyl-amine (0.220 g, 0.41 mol) and sodium bicarbonate (0.071 mg, 0.83 mol.) in methanol (8 mL) was stirred at 0° C. for 15 min. Cyanogen bromide (0.053 g, 0.05 mol) was added and continued to stir at room temperature for 1.5 h. Methanol was removed under reduced pressure, extracted with ethyl acetate (250 mL), washed with water (250 mL×2) and the organic layer was dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 0.220 g of colorless gummy compound.

Workup

stirringto stir at room temperature for 1.5 h
customMethanol was removed under reduced pressure
extractionextracted with ethyl acetate (250 mL)
washwashed with water (250 mL×2)
dry with materialthe organic layer was dried over anhydrous sodium sulfate
concentrationConcentration under reduced pressure

Sources & evidence

ORD record: ord-e622331ac5ce4cd1a1275d8dda873432
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604055B2

Reaction notes

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