Benzylamine → HCID 178503324, compound

HRID 1798906Notes

Reaction equation

HRID 1798906 reaction equation
[CH2:1]([N:8]1[C:18]2[C:19]3[C:11](=[N:12][NH:13][C:14]=3[N:15]=[C:16]([S:20][CH3:21])[N:17]=2)[CH:10]([C:22](O)=[O:23])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:25]([NH:32][C:22]([CH:10]1[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:18]2[C:19]3[C:11]1=[N:12][NH:13][C:14]=3[N:15]=[C:16]([S:20][CH3:21])[N:17]=2)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178503326HCID 178503326, compound

Product 1

HCID 178503324HCID 178503324, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Benzyl-7-(methylthio)-1,3,4,5-tetrahydro-1,2,5,6,8-pentaazaacenaphthylene-3-carboxlic acid (0.71 g, 2.1 mmol) and DMF (20 ml) were placed in a round-bottomed flask. To the stirring mixture was slowly added benzylamine (0.34 mL, 3.2 mmol), HBTU (1.03 g, 3.4 mmol), diisopropylethyl amine (1.1 mL, 6.3 mmol) and the solution was allowed to stir at room temperature for 16 h. The reaction was quenched by addition of EtOAc (200 mL) and washing with water (2×500 mL). The organic layer was combined, dried over MgSO4, and concentrated under reduced pressure to yield a yellow solid (0.84 g, 2.0 mmol). 1H-NMR (DMSO-d6): 8.56 (t, J=2.0 Hz, 1H), 7.40-7.22 (m, 10H), 4.36 (dd, J=8.1 & 21.2 Hz, 3H), 4.38-4.21 (m, 3H), 4.19 (t, J=5.2 Hz, 2H), 3.86-3.76 (m, 3H), 3.17 (d, J=5.2 Hz, 1H). LC: Rt=1.42 min. MS 431.53 [M+H].

Workup

  1. customThe reaction was quenched by addition of EtOAc (200 mL)
  2. washwashing with water (2×500 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-793d5487e50f41eea6473034b5d08ab4
Source dataset
uspto-grants-2013_01
Patent number
US08343983B2

Reaction notes

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