Dimethylformamide → 2-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid ((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-amide

HRID 1360728Notes

Reaction equation

HRID 1360728 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([NH:20]N)=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.N[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1O.[CH3:30][CH2:31]N(CC)CC.CN(C(ON1N=N[C:47]2[CH:48]=[CH:49][CH:50]=N[C:46]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN([CH:64]=[O:65])C>>[OH:65][C@@H:64]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:46]([NH:20][C:18]([C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[NH:10][C:11]=2[CH:17]=1)=[O:19])[C:47]1[CH:31]=[CH:30][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 232862-AminocyclohexanolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

Product 1

HCID 669667752-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid ((1R,2S)-2-hydroxy-1,2-diphenyl-ethyl)-amide

Procedure

To a 20 mL scint. vial was added 0.200 g (0.651 mmol) of Intermediate 1, 0.0825 g (0.716 mmol) of 2-amino cyclohexanol, 5 mL of DMF, 0.1815 mL (1.30 mmol) of Et3N, and 0.4952 g (1.3 mmol) of HATU. Allowed to stir at r.t. for 18 h. Extracted with EtOAc, washed with water, brine, and dried with Na2SO4. The title compound was prepared analogous to step A of Example 1-24. Used directly in next reaction. MS (m/z) 502.1 M (+1), tR=1.34, Meth 10

Workup

  1. extractionExtracted with EtOAc
  2. washwashed with water, brine
  3. dry with materialdried with Na2SO4
  4. customUsed directly in next reaction

Sources & evidence

ORD record
ord-8d212e71c8524b66b33b72d8abceb56b
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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