Bromobenzene → HCID 178434444, compound

HRID 2241264Notes

Reaction equation

HRID 2241264 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16](Cl)=[C:11]3[C:10]([CH3:18])=[N:9]2)=CC=1.[NH2:21][C:22]1[S:23][C:24]2[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:25]=2[N:26]=1.BrC1C=CC=CC=1>CN(C)C1C=CN=CC=1>[CH3:18][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[CH:15][C:16]=2[O:31][C:29]2[CH:28]=[CH:27][C:25]3[N:26]=[C:22]([NH2:21])[S:23][C:24]=3[CH:30]=2)[NH:8][N:9]=1

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 334622-Amino-6-benzothiazololHCID 685123991-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178434444HCID 178434444, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
150 °C

Procedure

A 20 mL sealable tube was charged with 1-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine (0.500 g, 1.74 mmol; prepared according to the procedure of Example 43, Step E), 2-aminobenzo[d]thiazol-6-ol (0.433 g, 2.61 mmol), N,N-dimethylpyridin-4-amine (0.0425 g, 0.348 mmol), and bromobenzene (4 mL). The reaction mixture was heated under nitrogen to 150° C. for 12 hours, then cooled to room temperature and concentrated under reduced pressure. The crude material was used directly in next step. LRMS (APCI pos) m/e 418.2 (M+1).

Workup

  1. customprepared
  2. temperaturecooled to room temperature
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a667827e538a4bf5b47db35cb2c2a4a9
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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