Boron tribromide → HCID 57463169, compound

HRID 1783819Notes

Reaction equation

HRID 1783819 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@@H:24]4[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C@@H:31]([OH:34])[CH2:32][OH:33])[CH2:25]4)[N:18]=2)[CH:14]=[CH:13][S:12]3)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[C:11]3[N:15]([C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C@@H:24]4[CH2:29][CH2:28][CH2:27][N:26]([CH2:30][C@@H:31]([OH:34])[CH2:32][OH:33])[CH2:25]4)[N:18]=2)[CH:14]=[CH:13][S:12]3)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57463168HCID 57463168, compound

Product 1

HCID 57463169HCID 57463169, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The (2R)-3-[(3R)-3-({4-[6-(3-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]pyrimidin-2-yl}amino)piperidin-1-yl]propane-1,2-diol (150 mg, 0.312 mmol) in methylene chloride (10 ml) was cooled to −78° C. and slowly treated with 1 molar solution of boron tribromide in methylene chloride (2.5 ml). The reaction mixture was kept at −78° C. for one hour then was allowed to warm to room temperature for 18 hours. The mixture was quenched by the addition of methanol (5 ml) at −78° C. and was stirred at room temperature for an additional hour. The mixture was concentrated in vacuo and the crude product was purified by flash chromatography (6:1 EtOAc/MeOH+drops of aq. NH4OH), affording the title compound as a pale yellow solid (71 mg, 49%). M.p.=185-187° C. 400 MHz 1H NMR (DMSO-d6) δ: 9.39 (s, 1H), 8.72 (br. s, 1H), 8.12 (d, J=5.1 Hz, 1H), 7.43 (d, J=4.4 Hz, 1H), 7.32 (br. s, 1H), 7.26-7.20 (m, 1H), 7.00-6.95 (m, 2H), 6.84-6.81 (m, 1H), 6.45 (d, J=5.5 Hz, 1H), 5.28-5.03 (br. s, 1H), 4.90-4.65 (br. s, 1H), 4.34-4.22 (m, 1H), 3.98-3.84 (m, 1H), 3.47-3.38 (m, 1H), 3.35-3.25 (m, 1H), 3.15-2.65 (m, 4H), 2.10-1.88 (m, 2H), 1.87-1.72 (m, 2H), 1.65-1.40 (m, 2H). LCMS: 467 [M+H].

Workup

  1. customThe mixture was quenched by the addition of methanol (5 ml) at −78° C.
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe crude product was purified by flash chromatography (6:1 EtOAc/MeOH+drops of aq. NH4OH)

Sources & evidence

ORD record
ord-18ed9a8a01804039ac8711f3f5f8358a
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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