Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 59451899, compound

HRID 1971254Notes

Reaction equation

HRID 1971254 reaction equation
[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([CH2:24][C:25](O)=[O:26])[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:28][C@@H:29]1[CH2:34][NH:33][CH2:32][CH2:31][NH:30]1.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.CCOC(C)=O.O>[C:1]12([CH2:11][NH:12][C:13]([C:15]3[N:20]4[CH:21]=[C:22]([CH2:24][C:25]([N:33]5[CH2:32][CH2:31][NH:30][C@H:29]([CH3:28])[CH2:34]5)=[O:26])[N:23]=[C:19]4[CH:18]=[CH:17][CH:16]=3)=[O:14])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

7

Reactant 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 73304342-Methylpiperazine, (R)-HCID 25270079HCID 25270079, compound

Product 1

HCID 59451899HCID 59451899, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of {5-[(adamantan-1-ylmethyl)-carbamoyl]-imidazo[1,2-a]pyridin-2-yl}-acetic acid (40 mg, 0.1 mmol) in DMF (1 mL) is sequentially added (R)-2-methyl-piperazine (43 mg, 0.44 mmol) and 96 mg of BOP (0.2 mmol). After stirring for 2 h at RT, the reaction mixture is diluted with EtOAc and water. The organic layer is separated, and the aqueous layer is back extracted with EtOAc. The combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. Purification of the residue by PTLC (10% MeOH, 1% NH4OH in DCM) affords the title compound.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is back extracted with EtOAc
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification of the residue by PTLC (10% MeOH, 1% NH4OH in DCM)

Sources & evidence

ORD record
ord-8148e98fa4c04ee9ab88b0e6393877ca
Source dataset
uspto-grants-2013_04
Patent number
US08431593B2

Reaction notes

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