Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 21945974, compound

HRID 2217010Notes

Reaction equation

HRID 2217010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]3=[C:15]([O:28][CH3:29])[C:16]([C:18]([NH:20][CH2:21][CH2:22][N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)=[O:19])=[CH:17][N:13]3[N:12]=[CH:11][N:10]=2)=[C:4]([F:30])[CH:3]=1.[CH3:31]NCCN1CCCC1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]3=[C:15]([O:28][CH3:29])[C:16]([C:18]([N:20]([CH3:31])[CH2:21][CH2:22][N:23]4[CH2:27][CH2:26][CH2:25][CH2:24]4)=[O:19])=[CH:17][N:13]3[N:12]=[CH:11][N:10]=2)=[C:4]([F:30])[CH:3]=1

Participants

5

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 295976Methyl(2-(pyrrolidin-1-yl)ethyl)amineHCID 21945976HCID 21945976, compound

Product 1

HCID 21945974HCID 21945974, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Compound A of Example 98 (20 mg, 0.052 mmol) in DMF (1 mL) was added 1-(2-methylaminoethyl)-pyrrolidine (10 mg, 0.078 mmol) and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (25 mg, 0.056 mmol). After 1 hr at 25° C. the mixture was purified directly by preparative HPLC, the product was collected, converted to its HCl salt and lyophilized to provide 22 mg (80%) of the title compound. MS: [M+H]+=491,493 (1:1);1H NMR (CD3OD): δ 8.27 (s, 1H), 7.83 (s, 1H), 7.73 (d, J=7.9 Hz, 1H), 7.65–7.55 (m, 2H), 4.09 (s, 3H), 3.99–3.96 (m, 4H), 3.85 (br s, 2H), 3.58–3.51 (m, 2H), 3.29–3.15 (m, 5H), 2.19–2.07 (m, 4H).

Workup

  1. customAfter 1 hr at 25° C. the mixture was purified directly by preparative HPLC
  2. customthe product was collected

Sources & evidence

ORD record
ord-c097db821f134091859b6870e7cb6f51
Source dataset
uspto-grants-2006_09
Patent number
US07112675B2

Reaction notes

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