Triethylamine → HCID 24860699, compound

HRID 1258461Notes

Reaction equation

HRID 1258461 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10]3[O:11][CH:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:13][CH2:14][C:15]=3[C:16]([C:18](O)=[O:19])=[CH:17][C:8]=2[N:7]=[C:6]1[CH3:27].[CH2:28]([N:30](CC)[CH2:31]C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.Cl.CNC>CN(C)C=O>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10]3[O:11][CH:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:13][CH2:14][C:15]=3[C:16]([C:18]([N:30]([CH3:31])[CH3:28])=[O:19])=[CH:17][C:8]=2[N:7]=[C:6]1[CH3:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67220219HCID 67220219, compound

Product 1

HCID 24860699HCID 24860699, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-methoxyethyl)-2-methyl-8-phenyl-1,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxylic acid (200 mg, 0.55 mmol, Step 12), triethylamine (0.30 mL, 2.18 mmol), and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (228 mg, 0.60 mmol) in N,N-dimethylformamide (5 mL) was added dimethylamine hydrochloride (49 mg, 0.60 mmol) at 0° C. After stirring at room temperature for 12 h, the mixture was poured onto water, and the aqueous layer was extracted with dichloromethane. The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (20:1) to afford the title compound as a white amorphous (215 mg, quant.).

Workup

  1. additionthe mixture was poured onto water
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (20:1)

Sources & evidence

ORD record
ord-95867aac19084ab5945ca30112d5a53f
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

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