Bis(2-amino-1H-imidazole) sulphate → HCID 18334319, compound

HRID 2297097Notes

Reaction equation

HRID 2297097 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][CH:9]=[N:10][C:6]2=[N:5][C:4]([CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22](OCC)=[O:23])=[CH:19][CH:20]=3)[CH:15]=[N:14]2)=[CH:3]1.[S:27]([OH:31])(O)(=O)=[O:28].NC1[NH:34][CH:35]=[CH:36][N:37]=1.[C:38]([O-:41])(=[O:40])C.[NH4+]>>[O:1]=[C:2]1[N:7]2[CH2:8][CH:9]=[N:10][C:6]2=[N:5][C:4]([CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]([NH:34][CH2:35][C@H:36]([NH:37][S:27]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)(=[O:31])=[O:28])[C:38]([OH:41])=[O:40])=[O:23])=[CH:19][CH:20]=3)[CH:15]=[N:14]2)=[CH:3]1

Participants

4

Reactant 3

HCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 517165Ammonium AcetateHCID 70155485HCID 70155485, compound

Product 1

HCID 18334319HCID 18334319, compoundYield 65%

Conditions

Temperature
150 °C

Procedure

1-(2-(5-Oxo-imidazo[1,2-a]pyrimidin-7-yl)ethyl)-5-ethoxycarbonylindazole. A mixture of the product prepared according to Example E-19 Part F (665 mg, 2.0 mmol), 2-aminoimidazole sulfate (291 mg, 2.2 mmol) and ammonium acetate (340 mg, 4.4 mmol) was heated on an oil bath at 150° C. After 2 h, the mixture was cooled and triturated in ethanol. The resulting solid was collected by filtration, washed with ethanol and dried to provide the title product (459 mg, 65%) as a gray-tan powder: 1H NMR (DMSO-d6) d 12.7 (bs, 1H), 8.44 (s, 1H), 8.25 (s, 1H), 7.88 (d, 1H), 7.71 (d, 1H), 7.52 (s, 1H), 7.47 (s, 1H), 5.69 (s, 1H), 4.80 (t, 2H), 4.32 (q, 2H), 3.10 (t, 2H), 1.33 (t, 3H); High resolution mass spectrum (NH3-CI) calculated (M+H+) 351.1331, found 351.1325.

Workup

  1. additionA mixture of the product
  2. customprepared
  3. temperaturethe mixture was cooled
  4. customtriturated in ethanol
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with ethanol
  7. customdried

Sources & evidence

ORD record
ord-e37f7314eab34e6c8db3413cc18fa6eb
Source dataset
uspto-grants-2002_12
Patent number
US06489333B2

Reaction notes

Loading…