Boron tribromide → HCID 57991613, compound

HRID 556114Notes

Reaction equation

HRID 556114 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([N:13]([CH2:17][CH2:18][OH:19])[CH2:14][CH2:15][OH:16])=[N:10][C:9]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[CH2:1]([C:8]1[S:12][C:11]([N:13]([CH2:17][CH2:18][OH:19])[CH2:14][CH2:15][OH:16])=[N:10][C:9]=1[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57991586HCID 57991586, compound

Product 1

HCID 57991613HCID 57991613, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A procedure similar to that in Example 74 was used. 2-[[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-(2-hydroxy-ethyl)-amino]-ethanol prepared in Example 73 and a solution of boron tribromide in dichloromethane were used as starting materials. The obtained crude product was recrystallized with acetone to give a product as a white solid in a yield of 54.7%, mp: 167-168 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 3.46 (2H, t, J=6.40 Hz, CH2), 3.59 (2H, t, J=6.40 Hz, CH2), 4.04 (2H, s, CH2), 4.88 (2H, t, J=5.20 Hz, 2×OH), 6.78 (2H, d, J=8.80 Hz, ArH), 7.15˜7.28 (5H, m, ArH), 7.36 (2H, d, J=8.80 Hz, ArH), 9.54 (1H, br, OH); EI-MS m/e (%): 370.1 (M+, 75), 339.1 (74), 309.0 (17), 295.0 (100); HREI-MS Calcd. for C20H22N2O3S: 370.1351. found: 370.1349. Anal. Calcd. for C20H22N2O3S: C, 64.84; H, 5.99; N, 7.56. found: C, 64.86; H, 5.89; N, 7.61.

Workup

  1. customThe obtained crude product
  2. customwas recrystallized with acetone

Sources & evidence

ORD record
ord-187e727bb4dc4a9a9fd45e7929cc86b2
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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