6-Bromopyrazolo[1,5-a]pyrimidine-2-carboxylic acid → HCID 71748081, compound

HRID 571645Notes

Reaction equation

HRID 571645 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Br:23][C:24]1[CH:25]=[N:26][C:27]2[N:28]([N:30]=[C:31]([C:33]([OH:35])=O)[CH:32]=2)[CH:29]=1.[N:36]1[C:41]2[CH2:42][CH2:43][NH:44][CH2:45][CH2:46][C:40]=2[CH:39]=[CH:38][CH:37]=1>CN(C=O)C>[Br:23][C:24]1[CH:25]=[N:26][C:27]2[N:28]([N:30]=[C:31]([C:33]([N:44]3[CH2:45][CH2:46][C:40]4[CH:39]=[CH:38][CH:37]=[N:36][C:41]=4[CH2:42][CH2:43]3)=[O:35])[CH:32]=2)[CH:29]=1

Participants

5

Reactant 3

HCID 7719386-Bromopyrazolo[1,5-a]pyrimidine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 231227435H,6H,7H,8H,9H-pyrido[2,3-d]azepine

Product 1

HCID 71748081HCID 71748081, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

73 mg (0.23 mmol) TBTU was added to 50 mg (0.21 mmol) 6-Bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid, 31 mg (0.21 mmol) 6,7,8,9-Tetrahydro-5H-pyrido[2,3-d]azepine and 90 μL (0.64 mmol) TEA in 1.5 mL DMF and stirred at RT overnight. The reaction mixture was purified by HPLC chromatography and lyophilized. Yield: 22 mg (29% of theory). ESI-MS: m/z=372 (M+H)+; Rt(HPLC): 0.81 min. (Method J).

Workup

  1. customThe reaction mixture was purified by HPLC chromatography

Sources & evidence

ORD record
ord-a27e939a9a584b5092e69d737c071641
Source dataset
uspto-grants-2015_05
Patent number
US09029360B2

Reaction notes

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