Boron tribromide → HCID 66688879, compound

HRID 337149Notes

Reaction equation

C([O:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([NH:21][C:22]1[C:23](=[O:42])[N:24]([C:28]2[CH:29]=[C:30]([CH:37]=[C:38]([F:41])[C:39]=2[CH3:40])[C:31]([NH:33][CH:34]2[CH2:36][CH2:35]2)=[O:32])[CH:25]=[CH:26][N:27]=1)([CH3:20])[CH3:19])C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[CH:34]1([NH:33][C:31](=[O:32])[C:30]2[CH:29]=[C:28]([N:24]3[CH:25]=[CH:26][N:27]=[C:22]([NH:21][C:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[S:11][CH2:10][CH2:9][OH:8])([CH3:20])[CH3:19])[C:23]3=[O:42])[C:39]([CH3:40])=[C:38]([F:41])[CH:37]=2)[CH2:36][CH2:35]1

Participants

Conditions

Temperature: 0 °C

Procedure

3-[3-{[1-(2-{[2-(Benzyloxy)ethyl]sulfanyl}phenyl)-1-methylethyl]amino}-2-oxopyrazin-1(2H)-yl]-N-cyclopropyl-5-fluoro-4-methylbenzamide (Example 320f, 1.2 g) was stirred in DCM (120 mL) and cooled to 0° C. Boron tribromide (0.387 mL of a 1M solution in DCM) was added dropwise at 0° C. and the reaction stirred for 30 min at 0° C. A further 4 eq of boron tribromide solution was added after 1 h and the reaction warmed to room temperature. The reaction mixture was diluted with ice water, and extracted with ethyl acetate. The organic layers were combined and dried (MgSO4), filtered and evaporated in vacuo to afford the crude product. The crude product was purified (SiO2 chromatography eluting with 100% diethyl ether to 100% ethyl acetate) to afford the subtitle compound as a solid (0.6 g).

Workup

temperaturethe reaction warmed to room temperature
extractionextracted with ethyl acetate
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated in vacuo
customto afford the crude product
customThe crude product was purified
wash(SiO2 chromatography eluting with 100% diethyl ether to 100% ethyl acetate)

Sources & evidence

ORD record: ord-b0185473bf2444c28646667b046bcc85
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889692B2

Reaction notes

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