Sodium Carbonate → 1-(6-(4-Pyrazolyl)-2-benzothiazolyl)-3-ethylurea

HRID 9147

Reaction equation

HRID 9147 reaction equation
NC1C=C(C2[CH:22]=[CH:21][C:11]3[N:12]=C(NC(NCC)=O)SC=3C=2)C=CC=1.Br[C:24]1[CH:38]=[CH:37][C:27]2[N:28]=[C:29]([NH:31][C:32]([NH:34][CH2:35][CH3:36])=[O:33])[S:30][C:26]=2[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].C[N:46](C=O)C.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:12]1[CH:11]=[C:21]([C:24]2[CH:38]=[CH:37][C:27]3[N:28]=[C:29]([NH:31][C:32]([NH:34][CH2:35][CH3:36])=[O:33])[S:30][C:26]=3[CH:25]=2)[CH:22]=[N:46]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 21962138N,N-Dimethylformamide--water (1/1)HCID 219855641-(6-Bromo-2-benzothiazolyl)-3-ethylureaHCID 219855751-(6-(3-Aminophenyl)-2-benzothiazolyl)-3-ethylurea

Product 1

HCID 219855781-(6-(4-Pyrazolyl)-2-benzothiazolyl)-3-ethylureaYield 30%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Similar to the synthesis of 1-(6-(3-aminophenyl)-2-benzothiazolyl)-3-ethylurea, a mixture of 4-pyrazolylboronic pinacolate, 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, sodium carbonate, and Pd(PPh3)4 in DMF/water mixed solvent was reacted to give the desired compound 0.543 g (30%). LC/MS 288.2 (M+1); LC retention time 2.61 min.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-a5f3ce06d6ac4f33ac47c498605c9889
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Linked notes

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