Hydrochloric Acid → Benzamide

HRID 1094743Notes

Reaction equation

HRID 1094743 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O1CCC[CH2:27][CH:26]1ON.CN1CC[O:37]CC1.Cl>CN1C(=O)CCC1.O.C(#N)C.CO>[C:14]([NH2:15])(=[O:37])[C:13]1[CH:27]=[CH:26][CH:10]=[CH:11][CH:12]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-Methylmorpholine2×HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To Int-3 (146 mg, 0.43 mmol) in NMP (6 mL) were added HATU (247 mg, 0.65 mmol), O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine (76 mg, 0.65 mmol) and NMM (0.15 mL, 1.3 mmol) and stirred. After 2 hours, additional O-(Tetrahydro-2H-pyran-2-yl)hydroxylamine (51 mg, 0.43 mmol), HATU (82 mg, 0.22 mmol) and NMM (0.1 mL) were added and stirred at room temperature for 1 hour. Then methanol (10 mL) and 1N HCl (12 mL) was added to the reaction mixture and stirred at room temperature for 1 hour. The reaction mixture was then diluted with water and acetonitrile and directly purified by preparative HPLC affording Compound 5 as tan solid, after lyophilization. MS found for C18H20N67O2 as (M+H)+ 353.2. 1H NMR (400 MHz, dmso-d6): δ 11.03 (s, 1H); 9.73 (s, 1H); 8.85 (s, 1H); 8.43 (d, J=5.2 Hz, 1H); 7.75 (d, J=8.8 Hz, 2H); 7.72 (d, J=8.8 Hz, 2H); 7.46 (s, 1H); 7.09 (d, J=5.2 Hz, 1H); 5.70 (m, 1H); 2.45 (s, 3H); 1.45 (d, J=6.8 Hz, 6H).

Workup

  1. stirringstirred at room temperature for 1 hour
  2. stirringstirred at room temperature for 1 hour
  3. customdirectly purified by preparative HPLC

Sources & evidence

ORD record
ord-00a5a9a4f4d54808a64e2cc0da695ec9
Source dataset
uspto-grants-2012_03
Patent number
US08134000B2

Reaction notes

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