Boron tribromide → HCID 57634115, compound

HRID 661107Notes

Reaction equation

[NH2:1][CH:2]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[C:23]([F:29])[CH:22]=1)[CH2:3][NH:4][C:5]1[S:6][C:7]([C:10]2[CH:19]=[CH:18][C:13]3[NH:14][C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)=[CH:8][N:9]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][CH:2]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([F:29])[CH:22]=1)[CH2:3][NH:4][C:5]1[S:6][C:7]([C:10]2[CH:19]=[CH:18][C:13]3[NH:14][C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)=[CH:8][N:9]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a 25 mL round-bottomed flask was added 6-(2-(2-amino-3-(3-fluoro-4-methoxyphenyl)propylamino)thiazol-5-yl)benzo[d]oxazol-2(3H)-one (Example 129) (60 mg, 145 μmol) and 3 mL of DCM. The solution was cooled to −78° C., and treated dropwise with boron tribromide, 1.0 M in DCM (497 μL, 2895 μmol) via a syringe. The solution was stirred at −78° C. for 1 hour and then allowed to warm to room temperature overnight. The reaction mixture was concentrated, and 2 mL of MeOH was added dropwise. The reaction mixture was purified by preparative LC to give 6-(2-(2-amino-3-(3-fluoro-4-hydroxyphenyl)propylamino)thiazol-5-yl)benzo[d]oxazol-2(3H)-one (20 mg, 35% yield). MS m/z: 401 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 2.85-2.98 (m, 2H), 3.47-3.53 (m, 1H), 3.62-3.71 (m, 2H), 6.92-6.97 (m, 2H), 7.05-7.10 (m, 2H), 7.26 (dd, J=8.02, 1.57 Hz, 1H), 7.37 (s, 1H), 7.38 (d, J=1.37 Hz, 1H).

Workup

temperatureto warm to room temperature overnight
concentrationThe reaction mixture was concentrated
addition2 mL of MeOH was added dropwise
customThe reaction mixture was purified by preparative LC

Sources & evidence

ORD record: ord-829a3c05fdd846269c35715afa4d2f17
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084479B2

Reaction notes

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