Boron tribromide → HCID 178432079, compound

HRID 1027251Notes

Reaction equation

C[O:2][C:3]1[C:4]([C:21]2[N:26]=[N:25][C:24]([N:27]([CH3:38])[CH:28]3[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]3)=[CH:23][CH:22]=2)=[CH:5][C:6]2[N:10]=[C:9]([CH3:11])[N:8](COCC[Si](C)(C)C)[C:7]=2[CH:20]=1.B(Br)(Br)Br>>[CH3:11][C:9]1[NH:8][C:7]2[CH:20]=[C:3]([OH:2])[C:4]([C:21]3[N:26]=[N:25][C:24]([N:27]([CH3:38])[CH:28]4[CH2:33][C:32]([CH3:35])([CH3:34])[NH:31][C:30]([CH3:37])([CH3:36])[CH2:29]4)=[CH:23][CH:22]=3)=[CH:5][C:6]=2[N:10]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 86710657HCID 86710657, compound

Product 1

HCID 178432079HCID 178432079, compoundYield 50%

Procedure

From 6-(6-methoxy-2-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-5-yl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (44 mg, 0.082 mmol), following General Method 3.2 for methoxy deprotection using BBr3, 2-methyl-5-(6-(methyl(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)-1H-benzo[d]imidazol-6-ol was obtained as a white solid after HPLC purification (16 mg, 50% yield). LCMS Rt=0.40 min [Method Q], MS (M+1)=395.4. 1H NMR (METHANOL-d4) δ 8.15 (d, J=10.1 Hz, 1H), 7.88 (s, 1H), 7.34 (d, J=9.6 Hz, 1H), 6.97 (s, 1H), 5.07 (t, J=11.9 Hz, 1H), 3.02 (s, 3H), 2.55 (s, 3H), 1.65-1.77 (m, 2H), 1.51-1.65 (m, 2H), 1.41 (s, 6H), 1.25 (s, 6H).

Sources & evidence

ORD record: ord-113989cae3314e4199fbe80cbc8f8a0b
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729263B2

Reaction notes

Loading…