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Hydrazine hydrate (1:1) → HCID 66799788, compound

HRID 528048
Notes
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Reaction equation

HRID 528048 reaction equation
[CH3:1][N:2]1[C:10]([C:11]([OH:13])=O)=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:14]1[CH2:19][CH2:18][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:16][CH2:15]1.CN(C(O[N:38]1[N:46]=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.O.NN>C(OCC)(=O)C.CN(C)C=O>[CH3:1][N:2]1[C:10]([C:11]([NH:38][NH2:46])=[O:13])=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:14]1[CH2:15][CH2:16][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:18][CH2:19]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66799955HCID 66799955, compound

Product 1

HCID 66799788HCID 66799788, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 10 mL round bottomed flask, 9-Methyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxylic acid (250 mg, 0.68 mmol, 1 equiv) and HATU (390 mg, 1.03 mmol, 1.5 equiv) were suspended anhydrous dimethylformamide (3 mL). Diisopropylethylamine (235 μL, 1.35 mmol, 2 equiv) followed by hydrazine monohydrate (330 μL, 6.81 mmol, 10 equiv) were added and the reaction stirred for one hour. The reaction mixture was diluted with ethyl acetate (20 mL), and the extracted with water (10 mL). The combined aqueous layer was then acidified with 1N aqueous hydrochloric acid to precipitate the desired product. This precipitate was filtered off, washed with water (2 mL) and acetonitrile (1 mL) and air dried yielding 115 mg of 9-methyl-6-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)-9H-purine-8-carbohydrazide, which was used directly in the next step.

Workup

  1. additionwere added
  2. extractionthe extracted with water (10 mL)
  3. customto precipitate the desired product
  4. filtrationThis precipitate was filtered off
  5. washwashed with water (2 mL) and acetonitrile (1 mL) and air
  6. customdried

Sources & evidence

ORD record
ord-ea8b9fe2c6ac4449a63496cdbf2465aa
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346807B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes