Methoxyacetic Acid → HCID 67314851, compound

HRID 1012767Notes

Reaction equation

HRID 1012767 reaction equation
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.[ClH:34].[NH2:35][C:36]1[CH:37]=[C:38]([C:42]2[C:50]3[S:49][C:48]([C:51]([NH:53][C@@H:54]4[CH:59]5[CH2:60][CH2:61][N:56]([CH2:57][CH2:58]5)[CH2:55]4)=[O:52])=[CH:47][C:46]=3[CH:45]=[CH:44][CH:43]=2)[CH:39]=[CH:40][CH:41]=1.[CH3:62][O:63][CH2:64][C:65](O)=[O:66]>CN(C=O)C>[ClH:34].[N:56]12[CH2:57][CH2:58][CH:59]([CH2:60][CH2:61]1)[C@@H:54]([NH:53][C:51]([C:48]1[S:49][C:50]3[C:42]([C:38]4[CH:39]=[CH:40][CH:41]=[C:36]([NH:35][C:65](=[O:66])[CH2:64][O:63][CH3:62])[CH:37]=4)=[CH:43][CH:44]=[CH:45][C:46]=3[CH:47]=1)=[O:52])[CH2:55]2

Participants

6

Reactant 4

HCID 12251Methoxyacetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67312996HCID 67312996, compound

Product 1

HCID 67314851HCID 67314851, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

96.4 mg (0.25 mmol) of HATU and 71.5 μl (0.41 mmol) of N,N-diisopropylethylamine are added to a solution of 50 mg (0.12 mmol) of 7-(3-aminophenyl)-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzothiophene-2-carboxamide hydrochloride (Example 81) and 18.5 μl (0.24 mmol) of methoxyacetic acid in 0.5 ml of DMF at 0° C. The mixture is stirred at room temperature for 3 h. Purification by preparative HPLC is followed by concentration of the product fractions and, after addition of a 3:1 mixture of acetonitrile and 1 N hydrochloric acid, concentration again. Drying under high vacuum results in 7 mg (11% of theory) of the title compound.

Workup

  1. customPurification by preparative HPLC
  2. additionafter addition of a 3:1 mixture of acetonitrile and 1 N hydrochloric acid, concentration again
  3. customDrying under high vacuum

Sources & evidence

ORD record
ord-1cf35d4f08ea41ca9feb84b0eefbe67c
Source dataset
uspto-grants-2011_07
Patent number
US07977485B2

Reaction notes

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