N,N-Dimethylethylenediamine → HCID 10452733, compound

HRID 856014Notes

Reaction equation

HRID 856014 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]3[CH:15]=[C:14]([C:16]4[N:21]=[C:20]([C:22]([OH:24])=O)[CH:19]=[CH:18][CH:17]=4)[CH:13]=[N:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[CH3:58][N:59]([CH3:63])[CH2:60][CH2:61][NH2:62].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:58][N:59]([CH3:63])[CH2:60][CH2:61][NH:62][C:22]([C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([C:14]2[CH:13]=[N:12][C:11]3[N:10]([N:9]=[CH:8][C:7]=3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:15]=2)[N:21]=1)=[O:24]

Participants

6

Reactant 4

HCID 66053N,N-DimethylethylenediamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 58691609HCID 58691609, compound

Product 1

HCID 10452733HCID 10452733, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)pyridine-2-carboxylic acid (6-1, 100 mg, 0.32 mmol, 1 equiv), benzotriazole-1-yl-oxy-trispyrrolidinophosphonium hexafluorophosphate (197 mg, 0.73 mmol, 1.2 equiv), N,N-dimethylethylenediamine (70 μL, 0.63 mmol, 2 equiv) and N,N-diisopropylethyl-amine (20 μL, 0.73 mmol, 2.3 equiv) in DMF (5 mL) was stirred at 23° C. for 3 hours. The solution was partitioned between EtOAc (3×100 mL) and water (120 mL). The combined organic layers were washed with brine (200 mL), dried over sodium sulfate, then concentrated to afford N-[2-(dimethylamino)ethyl]-6-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)pyridine-2-carboxamide (6-2). 1H NMR (500 MHz, DMSO-d6) δ 10.21 (s, 1 H), 9.72 (s, 1 H), 9.42 (m, 1 H), 8.91 (s, 1 H), 8.47 (m, 1 H), 8.08 (m, 3 H), 7.48 (m, 2 H), 7.29 (m, 1 H), 3.73 (m, 2 H), 3.36 (m, 2 H), 2.89 (s, 3 H), 1.74 (s, 3 H).

Workup

  1. customThe solution was partitioned between EtOAc (3×100 mL) and water (120 mL)
  2. washThe combined organic layers were washed with brine (200 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fb24a693e8e04a36bafbe355601e4fba
Source dataset
uspto-grants-2007_08
Patent number
US07262199B2

Reaction notes

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