Triethylamine → HCID 66904904, compound

HRID 1621050Notes

Reaction equation

HRID 1621050 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[CH:23]=[CH:22][C:7]2[CH:8]=[C:9]([C:11]([NH:13][C@@H:14]3[CH:19]4[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]4)[CH2:15]3)=[O:12])[S:10][C:6]=2[CH:5]=1.C(N(CC)CC)C.[CH:31]1([N:37]=[C:38]=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>C1COCC1.CN(C=O)C>[ClH:1].[N:16]12[CH2:21][CH2:20][CH:19]([CH2:18][CH2:17]1)[C@@H:14]([NH:13][C:11]([C:9]1[S:10][C:6]3[CH:5]=[C:4]([NH:3][C:38]([NH:37][CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[O:39])[CH:23]=[CH:22][C:7]=3[CH:8]=1)=[O:12])[CH2:15]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 66904443HCID 66904443, compound

Product 1

HCID 66904904HCID 66904904, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 40 mg (0.11 mmol) of 6-amino-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzothiophene-2-carboxamide dihydrochloride in 2 ml of THF and 0.2 ml of DMF is mixed with 29.8 μl (0.21 mmol) of triethylamine and 26.8 mg (0.21 mmol) of cyclohexyl isocyanate. After 18 h at room temperature, the product is purified by preparative HPLC. The concentrated product fraction is dissolved in a mixture of methanol and 1 N hydrochloric acid (2:1), again concentrated and dried under high vacuum. 23.4 mg (47.3% of theory) of the title compound are obtained.

Workup

  1. customthe product is purified by preparative HPLC
  2. dissolutionThe concentrated product fraction is dissolved in a mixture of methanol and 1 N hydrochloric acid (2:1)
  3. concentrationagain concentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-b89b337a82e84c70a1a01efd534f91b9
Source dataset
uspto-grants-2014_07
Patent number
US08772511B2

Reaction notes

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