Acetohydrazide → HCID 68298139, compound

HRID 528050Notes

Reaction equation

HRID 528050 reaction equation
[CH3:1][N:2]1[C:10]([C:11](O)=[O:12])=[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(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:63]([NH:66][NH2:67])(=[O:65])[CH3:64]>C(OCC)(=O)C.CC(N(C)C)=O>[C:63]([NH:66][NH:67][C:11]([C:10]1[N:2]([CH3:1])[C:3]2[C:8]([N:9]=1)=[C:7]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[O:29])[CH2:16][CH2:15]1)[N:6]=[CH:5][N:4]=2)=[O:12])(=[O:65])[CH3:64]

Participants

7

Reactant 4

HCID 14039AcetohydrazideHCID 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 68298139HCID 68298139, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

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 (185 mg, 0.51 mmol, 1 equiv) and HATU (290 mg, 0.76 mmol, 1.5 equiv) were suspended anhydrous DMA (2 mL). Diisopropylethylamine (175 μL, 1.0 mmol, 2 equiv) followed by acetic hydrazide (45 mg, 0.61 mmol, 1.2 equiv) were added and the reaction stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (20 mL), and the extracted with water (20 mL), and aqueous hydrochloric acid solution (0.1 M, 40 mL). The combined aqueous layers were then neutralized to pH=7 with saturated aqueous sodium bicarbonate. The resulting precipitate was filtered off, washed with water (2 mL) and acetonitrile (1 mL) and air dried yielding 135 mg of N′-acetyl-9-methyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carbohydrazide in 59% yield. 1H NMR (400 MHz, DMSO-d6) δ 10.82 (s, 1H), 9.91 (s, 1H), 8.29 (s, 1H), 7.18-7.08 (m, 1H), 6.87 (dt, 3H), 4.52 (t, 1H), 3.92 (d, 3H), 2.31 (s, 2H), 1.86 (s, 3H), 1.79 (d, 2H). MS (EI) for C21H23N9O3: 450 (MH+).

Workup

  1. additionwere added
  2. extractionthe extracted with water (20 mL), and aqueous hydrochloric acid solution (0.1 M, 40 mL)
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water (2 mL) and acetonitrile (1 mL) and air
  5. customdried

Sources & evidence

ORD record
ord-2404cb8076694491b9f3d2e9f099886e
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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