Boron tribromide → HCID 118483141, compound

HRID 1773353Notes

Reaction equation

HRID 1773353 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH2:30][CH2:31][CH2:32][O:33]C)[C:16](=[O:29])[CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([F:28])[CH:21]=3)[N:19]=2)[CH2:10][CH2:9]1)(C)(C)C.B(Br)(Br)Br>C(Cl)Cl>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:15]([CH2:30][CH2:31][CH2:32][OH:33])[C:16](=[O:29])[CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([F:28])[CH:21]=3)[N:19]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118483198HCID 118483198, compound

Product 1

HCID 118483141HCID 118483141, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {1-[4-(4-cyano-3-fluoro-phenyl)-1-(3-methoxy-propyl)-6-oxo-1,6-dihydro-pyrimidin-2-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester (200 mg, 0.41 mmol) in DCM was added 1M BBr3 (4 mL) at −78° C. The mixture was stirred at RT for 2 h and quenched at 0° C. with MeOH. The solution was washed with aqueous saturated NaHCO3. The organic layer was dried and concentrated. The residue was purified by preparative HPLC to give 35 mg of the title product as the hydrochloride salt (23%). 1H NMR (400 MHz, CD3OD): 1.65-1.69 (m, 2H), 1.97-2.19 (m, 4H), 3.13-3.22 (m, 2H), 3.48-3.55 (m, 1H), 3.73 (t, J=8.0 Hz, 2H), 4.55 (t, J=8.0 Hz, 2H), 4.94-4.95 (m, 2H), 6.71 (s, 1H), 7.88-8.05 (m, 3H). [M+H] Calc'd for C19H22FN5O2, 371. Found, 371.

Workup

  1. customquenched at 0° C. with MeOH
  2. washThe solution was washed with aqueous saturated NaHCO3
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-51e2f926a5c548458611a32402d4f72f
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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