Triethylamine → HCID 66904866, compound

HRID 1621049Notes

Reaction equation

HRID 1621049 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.[C:31]([N:35]=[C:36]=[O:37])([CH3:34])([CH3:33])[CH3:32]>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:36]([NH:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:37])[CH:23]=[CH:22][C:7]=3[CH:8]=1)=[O:12])[CH2:15]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 66904443HCID 66904443, compound

Product 1

HCID 66904866HCID 66904866, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 50 mg (0.13 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 37.2 μl (0.27 mmol) of triethylamine and 26.5 mg (0.27 mmol) of tert-butyl isocyanate. After 18 h at room temperature, the product is purified by preparative HPLC. The concentrated product fraction is dissolved in a mixture of acetonitrile and 1 N hydrochloric acid (5:1), again concentrated and dried under high vacuum. 19 mg (32.6% 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 acetonitrile and 1 N hydrochloric acid (5:1)
  3. concentrationagain concentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-a0752c5f7c3041df8a37a0dbb3e6ea2c
Source dataset
uspto-grants-2014_07
Patent number
US08772511B2

Reaction notes

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