Boron tribromide → HCID 57378611, compound

HRID 1802267Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:34]=[C:12]3[CH:13]=[C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:33])[N:22]=[CH:23][C:24]=4[C:25]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[O:26])=[O:19])[CH:15]=[CH:16][N:11]3[N:10]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl.O>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[N:34]=[C:12]3[CH:13]=[C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:33])[N:22]=[CH:23][C:24]=4[C:25]([N:27]4[CH2:28][CH2:29][O:30][CH2:31][CH2:32]4)=[O:26])=[O:19])[CH:15]=[CH:16][N:11]3[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-methyl-4-(morpholine-4-carbonyl)-2H-pyrazole-3-carboxylic acid [2-(3-methoxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide (Example 75) (2.7 g, 5.86 mmol) in DCM (50 ml) was added a solution of boron tribromide in DCM (1 M solution; 15 ml, 14.6 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 4 h under nitrogen atmosphere. The mixture was diluted with water (100 ml) and stirred for 15 min. The resultant precipitated solid was filtered, washed thoroughly with water and dried azeotropically with toluene (3×100 ml) to give 2-methyl-4-(morpholine-4-carbonyl)-2H-pyrazole-3-carboxylic acid [2-(3-hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-amide as off-white solid (2.5 g, 96%). LC-MS: m/z=448.4 [M+H]+.

Workup

stirringstirred for 15 min
customThe resultant precipitated solid
filtrationwas filtered
washwashed thoroughly with water
dry with materialdried azeotropically with toluene (3×100 ml)

Sources & evidence

ORD record: ord-2811d21e44a849d5b077bbf15bafc06d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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