HCID 178418600, compound → HCID 178488510, compound

HRID 1042002Notes

Reaction equation

HRID 1042002 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:20]3[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][C:23]=4[O:29][CH3:30])[N:9]=[C:10]([C@H:11]3[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.[NH2:31][C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:39])[NH2:38]>O.CCO>[NH2:31][C@H:32]([C:40]([OH:42])=[O:41])[CH2:33][CH2:34][CH2:35][NH:36][C:37](=[NH:38])[NH2:39].[NH2:1][C:2]1[C:7]2=[C:8]([C:20]3[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][C:23]=4[O:29][CH3:30])[N:9]=[C:10]([C@H:11]3[CH2:16][CH2:15][C@H:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 178418600HCID 178418600, compoundHCID 178488508HCID 178488508, compound

Product 1

HCID 178488510HCID 178488510, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

trans-4-[4-Amino-5-(7-methoxy-1H-indol-2-yl)-imidazo[5,1-f][1,2,4]triazin-7-yl]-cyclohexanecarboxylic acid (11.1 g, 27.4 mmol) and L-arginine (5.72 g, 32.9 mmol) were diluted with H2O (78.0 mL) and EtOH (78.0 mL). The suspension was heated to reflux to give a clear solution and then cooled to RT slowly. After 16 h, the suspension was cooled in an ice bath for 30 min and then filtered. The off-white solid was dried in vacuo at 80° C. for 2 days for provide the title compound (12.9 g, 81% yield). 1H NMR (400 MHz, CD3OD): δ 1.59-1.78 (m, 3H), 1.79-1.90 (m, 3H), 2.13 (br d, J=10.8 Hz, 4H), 2.35 (tt, J=12.4, 3.6 Hz, 1H), 3.20-3.42 (m, 1H), 3.37 (tt, J=12.0, 2.8 Hz, 1H), 3.66 (br s, 4H), 3.98 (s, 3H), 6.72 (d, J=7.6 Hz, 1H), 6.72 (s, 1H), 7.01 (dd, J=8.0, 8.0 Hz, 1H), 7.22 (d, J=8.4 Hz, 1H), 7.84 (s, 1H). X-ray powder diffraction analysis (XRPD) indicated that the salt is amorphous.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. customto give a clear solution
  4. temperaturethe suspension was cooled in an ice bath for 30 min
  5. filtrationfiltered
  6. customThe off-white solid was dried in vacuo at 80° C. for 2 days

Sources & evidence

ORD record
ord-332b157092084527a9f22541d54967fb
Source dataset
uspto-grants-2013_10
Patent number
US08557814B2

Reaction notes

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