Dimethylformamide → HCID 25262378, compound

HRID 1678432Notes

Reaction equation

HRID 1678432 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][N:19]([CH2:22][C:23](O)=[O:24])[CH2:18][CH2:17]2)[N:4]=1.[F:26][C:27]([F:37])([F:36])C1C=CC=CC=1CN.C([N:41]([CH:44](C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=2N=N1.CN(C=[O:78])C>>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)[N:6]=[C:5]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]([NH:41][CH2:44][C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=3[O:78][C:27]([F:26])([F:36])[F:37])=[O:24])[CH2:18][CH2:17]2)[N:4]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 764472-(Trifluoromethyl)benzylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67337738HCID 67337738, compound

Product 1

HCID 25262378HCID 25262378, compoundYield 20%

Procedure

To a solution of {-4-[4-(methylamino)-6-(4-methyl-1-piperazinyl)-1,3,5-triazin-2-yl]-1-piperazinyl}acetic acid (100 mg, 0.286 mmol, 1.00 equiv), {[2-(trifluoromethyl)phenyl]methyl}amine (48 μL, 0.34 mmol, 1.2 equiv), and diisopropylethylamine (DIEA, 75 μL, 0.43 mmol, 1.5 equiv) in DMF (1.8 mL) was added BOP (190 mg, 0.43 mmol, 1.5 equiv). The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was filtered and purified by reverse-phase HPLC (Sunfire, 10-80% CH3CN/H2O, 0.1% TFA, 15 min) to give 30 mg (20%) of the title compound. MS (ES+): m/e 524.2 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse-phase HPLC (Sunfire, 10-80% CH3CN/H2O, 0.1% TFA, 15 min)

Sources & evidence

ORD record
ord-daa647178dc348a299a5352600136b9c
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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