Triethylamine → HCID 59483855, compound

HRID 1808368Notes

Reaction equation

HRID 1808368 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][C:23]2[S:26][C:27]([C:29]([OH:31])=O)=[CH:28][C:22]=2[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].Cl.Cl.[N:34]1[CH:39]=[CH:38][C:37]([N:40]2[CH2:45][CH2:44][C:43]3([CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[CH2:42][CH2:41]2)=[CH:36][CH:35]=1.C(N(CC)CC)C>ClCCl.CN(C)C=O>[N:34]1[CH:35]=[CH:36][C:37]([N:40]2[CH2:45][CH2:44][C:43]3([CH2:46][CH2:47][N:48]([C:29]([C:27]4[S:26][C:23]5[CH2:24][CH2:25][N:20]([C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[CH2:21][C:22]=5[CH:28]=4)=[O:31])[CH2:49][CH2:50]3)[CH2:42][CH2:41]2)=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 177503995-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acidHCID 66701057HCID 66701057, compound

Product 1

HCID 59483855HCID 59483855, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

1,1′-Carbonyldiimidazole (119 mg, 0.741 mmol) and 5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid (200 mg, 0.706 mmol) were dissolved in dichloromethane (5 ml) and N,N-dimethylformamide (3 ml) and stirred for 1 h at room temperature. 3-(Pyridin-4-yl)-3,9-diazaspiro[5.5]undecane dihydrochloride (322 mg, 1.059 mmol), dissolved in a mixture of dichloromethane (5 ml) and triethylamine (0.293 ml, 2.118 mmol), was then added dropwise and the reaction mixture was stirred for 3 days at room temperature. The mixture was diluted with dichloromethane (50 ml) and washed with saturated sodium hydrogen carbonate solution (3×10 ml) and with saturated sodium chloride solution (10 ml), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol, 5:1). Yield: 280 mg (80%)

Workup

  1. additionwas then added dropwise
  2. washwashed with saturated sodium hydrogen carbonate solution (3×10 ml) and with saturated sodium chloride solution (10 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/methanol, 5:1)

Sources & evidence

ORD record
ord-5ccbbdd9e4ae49e3b1d9a92a745083ed
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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