2,4-Dichlorobenzylamine → HCID 25262079, compound

HRID 1678427Notes

Reaction equation

HRID 1678427 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[N:6]=[C:5]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=O)[CH2:18][CH2:17]2)[N:4]=1.[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[CH2:33][NH2:34].C(N(C(C)C)CC)(C)C.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>[Cl:25][C:26]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=1[CH2:33][NH:34][C:22]([CH:19]1[CH2:20][CH2:21][N:16]([C:5]2[N:4]=[C:3]([NH:2][CH3:1])[N:8]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)[N:6]=2)[CH2:17][CH2:18]1)=[O:24]

Participants

6

Reactant 4

HCID 14852,4-DichlorobenzylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67338791HCID 67338791, compound

Product 1

HCID 25262079HCID 25262079, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[4-(methylamino)-6-(4-methyl-1-piperazinyl)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid (84 mg, 0.25 mmol, 1.0 equiv), [(2,4-dichlorophenyl)methyl]amine (44 μL, 0.31 mmol, 1.3 equiv), and diisopropylethylamine (DIEA, 70 μL, 0.38 mmol, 1.5 equiv) in DMF (1.6 mL) was added BOP (166 mg, 0.38 mmol, 1.5 equiv). The reaction mixture was stirred overnight at room temperature. The resulting solution was filtered and purified using reverse-phase HPLC (Sunfire, 10-45% CH3CN/H2O, 0.1% TFA, 12 min) to afford 28 mg (23%) of the title compound. MS (ES+): m/e 493.1 [M]+.

Workup

  1. filtrationThe resulting solution was filtered
  2. custompurified
  3. customreverse-phase HPLC (Sunfire, 10-45% CH3CN/H2O, 0.1% TFA, 12 min)

Sources & evidence

ORD record
ord-934ac127397341c2a1ce5ffa44d6687b
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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