Triethylamine → N-[2-(1-methylpyrrolidin-2-yl)ethyl]-1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 928583Notes

Reaction equation

HRID 928583 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2[C:19]3[C:18]([N:20]4[CH2:25][CH2:24][CH:23]([C:26](O)=[O:27])[CH2:22][CH2:21]4)=[N:17][CH:16]=[N:15][C:14]=3[S:13][CH:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:29][N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[CH2:35][CH2:36][NH2:37].C(N(CC)CC)C>C(Cl)Cl>[CH3:29][N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[CH2:35][CH2:36][NH:37][C:26]([CH:23]1[CH2:22][CH2:21][N:20]([C:18]2[C:19]3[C:11]([C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:12][S:13][C:14]=3[N:15]=[CH:16][N:17]=2)[CH2:25][CH2:24]1)=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 2796111HCID 2796111, compound

Product 1

HCID 89579749N-[2-(1-methylpyrrolidin-2-yl)ethyl]-1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (26 μL, 0.35 mmol) was added to (1-(5-phenylthieno[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid (100 mg, 0.294 mmol) in dry DCM at 0° C. The reaction was stirred for 30 min then 2-(1-methylpyrrolidin-2-yl)ethanamine (173 μL, 0.294 mmol) and triethylamine (82 μL, 0.588 mmol) were added and the reaction stirred for a further 10 min at 0° C. and then stirred at room temperature for 1 hr. The reaction was reduced to dryness in vacuo and the residue purified by prep HPLC (Basic, method F) to give the desired compound as an off-white solid. Yield=70 mg. LCMS [M+H]+=450; RT=3.01 min

Workup

  1. stirringthe reaction stirred for a further 10 min at 0° C.
  2. stirringstirred at room temperature for 1 hr
  3. customthe residue purified by prep HPLC (Basic, method F)

Sources & evidence

ORD record
ord-7348a947deb84174b8638b816401c00b
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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