Triethylamine → HCID 58727740, compound

HRID 1992226Notes

Reaction equation

HRID 1992226 reaction equation
Cl.Cl.[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3([CH2:18][CH2:19][N:20]4[CH:25]5[CH2:26][CH2:27][CH:21]4[CH2:22][CH:23]([N:28]4[C:32]6[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=6[N:30]=[C:29]4[CH3:37])[CH2:24]5)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:11][C:6]=2[O:5][CH2:4]1.C(N(CC)CC)C.[OH:45][C:46]([CH3:51])([CH3:50])[C:47](O)=[O:48].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3([CH2:18][CH2:19][N:20]4[C@H:25]5[CH2:26][CH2:27][C@@H:21]4[CH2:22][CH:23]([N:28]4[C:32]6[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=6[N:30]=[C:29]4[CH3:37])[CH2:24]5)[CH2:13][CH2:14][N:15]([C:47](=[O:48])[C:46]([CH3:51])([OH:45])[CH3:50])[CH2:16][CH2:17]3)=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 116712-Hydroxyisobutyric acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68677071HCID 68677071, compound

Product 1

HCID 58727740HCID 58727740, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(8-{2-[4-(1,3-benzodioxol-5-yl)piperidin-4-yl]ethyl}-8-azabicyclo[3.2.1]oct-3-yl)-2-methyl-1H-benzimidazole dihydrochloride (0.20 g, 0.39 mmol), triethylamine (0.17 mL, 1.25 mmol) and 2-hydroxyisobutyric acid (41 mg, 0.39 mmol) in dimethylformamide (1.25 mL) was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (163 mg, 0.43 mmol) and the resulting mixture was stirred for 1 h at rt. The mixture was diluted with water and the resulting precipitate was collected, washed with saturated sodium bicarbonate solution, with water, dried and purified by chromatography on silica gel eluting with a dichloromethane to methanol-dichloromethane 1:19 gradient to give 1-(4-(1,3-benzodioxol-5-yl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}piperidin-1-yl)-2-methyl-1-oxopropan-2-ol as a solid (0.10 g, 44%). HRMS C33H42N4O4 m/z 559.3284 (M+H)Cal. 559.3276 (M+H)Obs..

Workup

  1. customthe resulting precipitate was collected
  2. washwashed with saturated sodium bicarbonate solution, with water
  3. customdried
  4. custompurified by chromatography on silica gel eluting with a dichloromethane to methanol-dichloromethane 1:19 gradient

Sources & evidence

ORD record
ord-707d882fe8fe4818ac9c6fcacc63aae2
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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