Diisopropylethylamine → HCID 67314100, compound

HRID 1012709Notes

Reaction equation

HRID 1012709 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6]2[CH:7]=[C:8]([C:10]([OH:12])=O)[S:9][C:5]=2[CH:4]=1)#[N:2].[ClH:15].Cl.[NH2:17][C@@H:18]1[CH:23]2[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]2)[CH2:19]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[ClH:15].[N:20]12[CH2:25][CH2:24][CH:23]([CH2:22][CH2:21]1)[C@@H:18]([NH:17][C:10]([C:8]1[S:9][C:5]3[CH:4]=[C:3]([C:1]#[N:2])[CH:14]=[CH:13][C:6]=3[CH:7]=1)=[O:12])[CH2:19]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 106796506-Cyanobenzo[b]thiophene-2-carboxylic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

Product 1

HCID 67314100HCID 67314100, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

320.8 mg (1.1 mmol) of 6-cyano-1-benzothiophene-2-carboxylic acid (Example 25A), 200 mg (1.0 mmol) of (R)-3-aminoquinuclidine dihydrochloride, 458.3 mg (1.21 mmol) of HATU, 467.3 mg (3.62 mmol) of N,N-diisopropylethylamine and 4.0 ml of DMF are reacted by general method C. The reaction mixture is purified by preparative HPLC. The product is dissolved in a mixture of methanol and 4 M hydrogen chloride in dioxane and then concentrated and dried under high vacuum. 222.1 mg (64% of theory) of the title compound are obtained.

Workup

  1. customThe reaction mixture is purified by preparative HPLC
  2. dissolutionThe product is dissolved in a mixture of methanol and 4 M hydrogen chloride in dioxane
  3. concentrationconcentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-f6902573fb3244c795a6e9406341a0e4
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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