Triethylamine → HCID 58980933, compound

HRID 1181791Notes

Reaction equation

HRID 1181791 reaction equation
Cl.[NH2:2][OH:3].[Cl:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:14][N:15]1[C:23]([C:24]2[N:25]([CH3:35])[CH:26]=[C:27]([C:29](=O)[C:30]([F:33])([F:32])[F:31])[CH:28]=2)=[C:22]2[C:17]([N:18]([CH2:39][CH:40]3[CH2:42][CH2:41]3)[C:19](=[O:38])[N:20]([CH3:37])[C:21]2=[O:36])=[N:16]1.C(N(CC)CC)C>CC(N(C)C)=O>[Cl:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH2:14][N:15]1[C:23]([C:24]2[N:25]([CH3:35])[CH:26]=[C:27](/[C:29](=[N:2]/[OH:3])/[C:30]([F:33])([F:32])[F:31])[CH:28]=2)=[C:22]2[C:17]([N:18]([CH2:39][CH:40]3[CH2:42][CH2:41]3)[C:19](=[O:38])[N:20]([CH3:37])[C:21]2=[O:36])=[N:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochloride2×HCID 58980979HCID 58980979, compound

Product 1

HCID 58980933HCID 58980933, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

Hydroxylamine hydrochloride (0.062 g) was added to a solution of 2-[(5-chloro-1H-indol-3-yl)methyl]-7-(cyclopropylmethyl)-5-methyl-3-[1-methyl-4-(trifluoroacetyl)-1H-pyrrol-2-yl]-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (0.05 g) and triethylamine (0.063 ml) in dimethylacetamide (5 ml) and the mixture heated at 80° C. for 2 hours. Additional hydroxylamine hydrochloride (0.062 g) was added and the reaction continued at 80° C. for another 3 hours. Cooled, concentrated, and the crude residue purified on preparative HPLC to give the title compound (0.015 g). Mass: 574.17 (M+H).

Workup

  1. temperatureCooled
  2. concentrationconcentrated
  3. customthe crude residue purified on preparative HPLC

Sources & evidence

ORD record
ord-e598c47d0f144071bc5eb00103499825
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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