Dichloromethane → HCID 68157708, compound

HRID 243197Notes

Reaction equation

HRID 243197 reaction equation
C(OC([NH:8][C@H:9]([C:11]1[N:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13]2[C:19]([C:20]([OH:22])=O)=[C:18]([F:23])[CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:10])=O)(C)(C)C.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(Cl)[Cl:61]>C([O-])(O)=O.[Na+]>[ClH:61].[ClH:61].[NH2:8][C@H:9]([C:11]1[N:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13]2[C:19]([C:20]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:22])=[C:18]([F:23])[CH:17]=[CH:16][C:14]=2[N:15]=1)[CH3:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68158022HCID 68158022, compound

Product 1

HCID 68157708HCID 68157708, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-((S)-1-tert-butoxycarbonylaminoethyl)-5-fluoro-3-phenyl-3H-benzoimidazole-4-carboxylic acid (279 mg, 0.69 mmol) and morpholine (244 μL, 2.80 mmol) in DCM (5 mL) was added HATU (398 mg, 1.05 mmol) and the reaction stirred at RT for 1 h. The reaction mixture was diluted with sat. aq. NaHCO3 and extracted with DCM (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4), and concentrated in vacuo to give the product as yellow oil. LCMS (Method C): RT=3.01 min, [M+H]+=469. The product was dissolved in HCl in dioxane (4N, 10 mL) and the reaction mixture stirred at RT for 30 min. The reaction mixture was concentrated in vacuo to give the product as an off white solid. LCMS (Method C): RT=0.27 min, [M+H]+=369.

Workup

  1. extractionextracted with DCM (3×10 mL)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-158e5e95f14b4bd691d58969d84337bd
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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