Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86711711, compound

HRID 528031Notes

Reaction equation

HRID 528031 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.CCN(C(C)C)C(C)C.Cl.[CH3:40][NH:41][O:42][CH3:43].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O.ClCCl>[CH3:43][O:42][N:41]([CH3:40])[C:11]([C:10]1[N:2]([CH3:1])[C:3]2[C:8]([N:9]=1)=[C:7]([N:14]1[CH2:15][CH2:16][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])[CH2:18][CH2:19]1)[N:6]=[CH:5][N:4]=2)=[O:13]

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (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 86711711HCID 86711711, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

9-Methyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxylic acid (450 mg, 1.14 mmol) was dissolved in dimethylacetamide (3 mL) and DIPEA (0.57 mL, 3.43 mmol). N,O-Dimethylhydroxylamine hydrochloride salt (123 mg, 1.26 mmol) was added to the solution, followed by dichloromethane (3 mL) and HATU (522 mg, 1.37 mmol). The reaction was stirred at room temperature for 1 hour. The crude reaction mixture was concentrated, diluted with 80 mL of dichloromethane, was washed with 2×50 mL of water and 3×50 mL of saturated potassium carbonate. The organic layer was collected, dried over magnesium sulfate, was filtered and was concentrated to afford N-methoxy-N,9-dimethyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxamide (quantitative yield) as an oil. 1H NMR (400 MHz, DMSO-d6): δ 10.84 (s, 1H), 8.32 (s, 1H), 7.18-7.12 (m, 1H), 6.96-6.88 (m, 3H), 5.38 (br s, 2H), 4.55 (tt, 1H), 3.76 (s, 3H), 3.75 (s, 3H), 3.49-3.09 (m, 5H), 2.40-2.23 (m, 2H), 1.83 (br d, 2H). MS (EI) for C21H24N8O3: 437 (MH+).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated
  3. additiondiluted with 80 mL of dichloromethane
  4. washwas washed with 2×50 mL of water and 3×50 mL of saturated potassium carbonate
  5. customThe organic layer was collected
  6. dry with materialdried over magnesium sulfate
  7. filtrationwas filtered
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-ba246f7716464d8985964e09814bc975
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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