Hydrochloric Acid → HCID 68425729, compound

HRID 1163089Notes

Reaction equation

HRID 1163089 reaction equation
[O:1]1CCC[CH2:3][CH:2]1[O:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH2:19][C:20]1[CH:37]=[CH:36][C:23]([C:24]([N:26]2[CH2:30][CH2:29][C@H:28]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[CH2:27]2)=[O:25])=[CH:22][CH:21]=1.Cl.C([O:41][CH2:42][CH3:43])C.C([OH:46])C>>[C:42]([OH:41])(=[O:46])/[CH:43]=[CH:3]/[C:2]([OH:7])=[O:1].[N:31]1([C@H:28]2[CH2:29][CH2:30][N:26]([C:24]([C:23]3[CH:36]=[CH:37][C:20]([CH2:19][C:11]4[N:10]([CH2:9][CH2:8][OH:7])[C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=5[N:12]=4)=[CH:21][CH:22]=3)=[O:25])[CH2:27]2)[CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21585056Diethyl ether ethanolHCID 58970774HCID 58970774, compound

Product 1

HCID 68425729HCID 68425729, compound

Procedure

Using essentially the same procedure described for Examples 217-222 and employing methyl 4-((1H-benzo[d]imidazol-2-yl)methyl)benzoate and 2-(2-bromoethoxy)tetrahydro-2H-pyran as starting materials, (3′S)-1′-{4-[(1-(2-(tetrahydro-pyran-2-yloxy)-ethyl)-1H-benzimidazol-2-yl)methyl]benzoyl}-1,3′-bipyrrolidine was obtained, [M+H] 503.2. A portion of (3′S)-1′-{4-[(1-(2-(tetrahydro-pyran-2-yloxy)-ethyl)-1H-benzimidazol-2-yl)methyl]benzoyl}-1,3′-bipyrrolidine was treated with hydrogen chloride in diethyl ether/ethanol, stirred at room temperature and concentrated in vacuo. The resultant residue was partitioned between aqueous potassium carbonate (1.0 M) and dichloromethane. The organic phase was separated, washed with water, dried over sodium sulfate and concentrated under reduced pressure. This residue was treated with fumaric acid in dichloromethane/methanol to give the title product. 1H NMR (300 MHz, DMSO-d6+TFA): 7.94 (m, 1 H), 7.79 (m, 1 H), 7.57 (d, 2 H), 7.57 (m, 2 H), 7.49 (d, 2 H), 6.65 (s, 2 H), 4.74 (s, 2 H), 4.58 (t, 2 H), 3.92 (m, 2 H), 3.80 (t, 2 H), 3.74 (m, 2 H), 3.51 (m, 2 H), 3.44-3.06 (br. s, 3 H), 2.33 (m, 1 H), 2.21 (m, 1 H), 1.99 (m, 4 H). [M+H] 419.17.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was partitioned between aqueous potassium carbonate (1.0 M) and dichloromethane
  3. customThe organic phase was separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionThis residue was treated with fumaric acid in dichloromethane/methanol

Sources & evidence

ORD record
ord-256576445e9f4a29ac1c6f55abd4de9a
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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