Boron tribromide → HCID 57991593, compound

HRID 556113Notes

Reaction equation

HRID 556113 reaction equation
[CH2:1]([C:8]1[S:12][C:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[N:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=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]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)=[N:10][C:9]=1[C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23655018HCID 23655018, compound

Product 1

HCID 57991593HCID 57991593, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A procedure similar to that in Example 74 was used. 1-[5-benzyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-piperazine prepared in Example 71 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 49.2%, mp: 222-223 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 2.71 (2H, s, CH2), 3.20 (2H, m, CH2), 3.40 (1H, br, NH), 4.01 (2H, s, CH2), 6.70 (2H, d, J=8.00 Hz, ArH), 7.05˜7.25 (2H, m, ArH), 7.31 (2H, d, J=8.00 Hz, ArH), 9.48 (1H, s, OH); EI-MS m/e (%): 351.1 (M+, 77), 309.0 (29), 295.0 (100), 282.0 (42); HREI-MS Calcd. for C20H21N3OS: 351.1405. found: 351.1406.

Workup

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

Sources & evidence

ORD record
ord-44bd6fcbd7264d13bdccd0bc3bf10034
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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