HCID 67199810, compound → HCID 86621654, compound

HRID 547565Notes

Reaction equation

HRID 547565 reaction equation
[ClH:1].[NH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16]C(=O)C)=[CH:12][CH:11]=2)[CH:6]=[C:5]([CH3:20])[N:4]=1>Cl>[ClH:1].[NH2:16][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:7]2[CH:6]=[C:5]([CH3:20])[N:4]=[C:3]([NH2:2])[N:8]=2)=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 67199810HCID 67199810, compound

Product 1

HCID 86621654HCID 86621654, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 16 (6.0 g, 20 mmol) was added 2N HCl (40 mL) and the mixture was refluxed for 20 h. The solvents were evaporated to dryness, residue boiled in MeOH and diluted with EtOAc. The resulting precipitate was filtered and washed with EtOAc and dried to give essentially pure 17 (5.0 g, 97%); mp (MeOH/EtOAc) 275-280° C.; 1H NMR [(CD3)2SO] δ 12.50 (br, 1 H, N+H), 10.75 (br s, 1 H, NH), 9.75 (br s, 2 H, NH2), 7.85 (br s, 4 H, NH2 & ArH)), 7.34 (d, J=8.6 Hz, 2 H, ArH), 6.24 (br s, 1 H, ArH), 2.79 (s, 3 H, CH3), HRMS (FAB+) calc. for C11H14N5 (M+1) m/z 216.1249, found 216.1247.

Workup

  1. temperaturethe mixture was refluxed for 20 h
  2. customThe solvents were evaporated to dryness, residue
  3. additiondiluted with EtOAc
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with EtOAc
  6. customdried

Sources & evidence

ORD record
ord-dc63f2df74344b81bdaad353d1faac06
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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