Water → HCID 178508868, compound

HRID 2059763Notes

Reaction equation

HRID 2059763 reaction equation
O=[C:2]1[C:8]2([CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:17]([O:19]C)=O.[N+]([O-])(O)=O.[NH2:25][C:26]([NH2:28])=[NH:27].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(O)(=O)C>[NH2:28][C:26]1[N:25]=[C:17]([OH:19])[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:8]3([CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9]3)[C:2]=2[N:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10481Guanidine NitrateHCID 11430Potassium CarbonateHCID 68800424HCID 68800424, compound

Product 1

HCID 178508868HCID 178508868, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 19B (490 mg, 1.799 mmol), guanidine nitrate (439 mg, 3.60 mmol), and potassium carbonate (497 mg, 3.60 mmol) in DMF (4 mL) was heated overnight at 120° C. After this time, the mixture was cooled to room temperature, then poured into 50 mL of water. The pH was adjusted to about 5 with acetic acid, then the precipitate was collected by filtration, washed with water, and air-dried. The sample was further dried azeotropically with toluene to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ 10.70 (br, 1H), 7.07-7.20 (m, 4H), 6.14 (br s, 2H), 3.58 (d, J=16.0 Hz, 2H), 2.95 (m, 1H), 2.90 (m, 1H), 2.57-2.66 (m, 2H), 1.59-1.74 (m, 4H), 1.49 (m, 2H). MS (DCI+) m/z 282 (M+H).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. customair-dried
  4. dry with materialThe sample was further dried azeotropically with toluene

Sources & evidence

ORD record
ord-134fbaf34945423284d5896b1320b0dd
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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