Dimethylformamide → HCID 67496741, compound

HRID 1628268Notes

Reaction equation

HRID 1628268 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)=[CH:3][CH:2]=1.CN(C(ON1N=N[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:40](C(C)C)[CH:41]([CH3:43])[CH3:42].CN(C=[O:51])C>>[NH2:40][C@@H:41]([CH2:43][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:42]([NH:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:8]=1)=[O:51]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 4595233-(4-Pyridyl)anilineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67496741HCID 67496741, compound

Procedure

To a 100 ml flask was added 3-(pyridin-4-yl)benzenamine 34.1.C. (500 mg, 2.9 mole), HBTU (1300 mg, 3.5 mmole), n-(tert-butoxycarbonyl)-1-phenylalanine (858 g, 3.2 mmole), 20 ml of DMF and DIEA (756 ul, 4.35 mmole). The reaction was stirred at room temperature for 6 hours, at which time the crude reaction was purified with a silica gel column (eluting with 10% MeOH in DCM) to give (S)-2-amino-3-phenyl-N-(3-(pyridin-4-yl)phenyl)propanamide.

Workup

  1. customreaction
  2. customwas purified with a silica gel column (eluting with 10% MeOH in DCM)

Sources & evidence

ORD record
ord-95838aff0faa4f699a1f4c945b19f793
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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