Boron tribromide → N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4-dihydroxy-benzamide

HRID 556082Notes

Reaction equation

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

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 57991617N-[5-cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide

Product 1

HCID 57991599N-[5-cyclohexylmethyl-4-(4-hydroxy-phenyl)-thiazol-2-yl]-3,4-dihydroxy-benzamideYield 60.5%

Procedure

A procedure similar to that in Example 7 was used. N-[5-cyclohexylmethyl-4-(4-methoxy-phenyl)-thiazol-2-yl]-3,4-dimethoxy-benzamide prepared in Example 48 and boron tribromide were used as starting materials. The obtained crude product was recrystallized with ethyl acetate to obtain a product as a white solid in a yield of 60.5%, mp: 133-134 └. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.75˜0.90 (2H, m), 0.95˜1.18 (3H, m), 1.15˜1.17 (6H, m), 2.65 (2H, d, J=7.0 Hz), 6.75 (1H, d, J=8.0 Hz, ArH), 6.76 (2H, d, J=8.4 Hz, ArH), 7.32 (2H, d, J=8.4 Hz, ArH), 7.41 (1H, d, J=2.4 Hz, ArH), 7.46 (1H, dd, J=8.4, 2.4 Hz, ArH), 9.52 (1H, br, OH), 12.15 (1H, br, CONH); EI-MS m/e (%): 424.1 (M+, 21), 288.1 (36), 205.1 (100); HREI-MS Calcd. for C23H24N2O4S: 424.1457. found: 424.1458.

Workup

customThe obtained crude product
customwas recrystallized with ethyl acetate

Sources & evidence

ORD record: ord-8871b041f81249b697e6fc67cfa96de2
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053581B2

Reaction notes

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