Hydrochloric Acid → HCID 66810908, compound

HRID 1486775Notes

Reaction equation

HRID 1486775 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]2[C:20]3[N:19]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[NH:17][C:16]=3[CH:15]=[CH:14][CH:13]=2)=[O:11])[CH2:4][CH2:3]1.C(N(CC)C(C)C)(C)C.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][CH:44]([CH:47]=O)[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][CH:44]([CH2:47][N:2]2[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]([C:12]3[C:20]4[N:19]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[NH:17][C:16]=4[CH:15]=[CH:14][CH:13]=3)=[O:11])[CH2:4][CH2:3]2)[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 66811036HCID 66811036, compound

Product 1

HCID 66810908HCID 66810908, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of the bis HCl salt of 2-tert-butyl-1H-benzoimidazole-4-carboxylic acid (piperidin-4-ylmethyl)amide (4.28 g, 11.06 mmol) in dichloromethane (55 mL) at room temperature was added N,N-diisopropylethylamine (1.71 g, 2.31 mL), 1-(tert-butoxycarbonyl)piperidine-4-carboxaldehyde (2.58 g, 12.17 mmol) and sodium triacetoxyborohydride (3.28 g, 15.48 mmol) sequentially. The resulting mixture was stirred at room temperature for 2 h then extracted with 1M aqueous hydrochloric acid. The combined aqueous layers were basified to pH 12 with sodium hydroxide pellets, then extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The resulting residue was dried under high vacuum to give a light brownish foam (4.9 g, 9.6 mmol, 87%) which was used without further purification. (m/z): [M+H]+ calcd for C29H45N5O3 512.35. found: 512.4.

Workup

  1. extractionthen extracted with 1M aqueous hydrochloric acid
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was dried under high vacuum

Sources & evidence

ORD record
ord-5671adb85cd44391bb85ac1b2e1c34a1
Source dataset
uspto-grants-2016_08
Patent number
US09428489B2

Reaction notes

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