Hydrochloric Acid → HCID 178423523, compound

HRID 717154Notes

Reaction equation

HRID 717154 reaction equation
Cl.O.FC(F)(F)C(O)=O.[CH3:10][C:11]1[CH:16]=[C:15]([C:17]2[N:21](C3CCCCO3)[CH:20]=[N:19][N:18]=2)[CH:14]=[CH:13][C:12]=1[C:28]1[N:33]=[C:32]2[NH:34][C:35]3([CH2:40][CH2:39]3)[C:36](=[O:38])[NH:37][C:31]2=[N:30][CH:29]=1>C(O)C>[CH3:10][C:11]1[CH:16]=[C:15]([C:17]2[NH:21][CH:20]=[N:19][N:18]=2)[CH:14]=[CH:13][C:12]=1[C:28]1[N:33]=[C:32]2[NH:34][C:35]3([CH2:39][CH2:40]3)[C:36](=[O:38])[NH:37][C:31]2=[N:30][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 666081077'-(2-Methyl-4-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-1'H-spiro[cyclopropane-1,2'-pyrazino[2,3-b]pyrazin]-3'(4'H)-one trifluoroacetate

Product 1

HCID 178423523HCID 178423523, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6 N Hydrochloric acid in water (0.171 mL, 1.025 mmol) was added to a stirred mixture of 7′-(2-methyl-4-(4-(tetrahydro-2H-pyran-2-yl)-4H-1,2,4-triazol-3-yl)phenyl)-1′H-spiro[cyclopropane-1,2′-pyrazino[2,3-b]pyrazin]-3′(4′H)-one trifluoroacetate (0.109 g, 0.205 mmol) in ethanol (4 mL) at 80° C. The resulting mixture was stirred vigorously and heated at 80° C. under a reflux condenser under nitrogen for 30 min. The resulting mixture was filtered and purified using reverse-phase preparatory HPLC (10-60% acetonitrile+0.1% TFA in water+0.1% TFA, over 30 min). Fractions containing the desired product were combined, neutralized with saturated aqueous sodium bicarbonate and most of the solvent removed under reduced pressure. Solids were collected by vacuum filtration, washed thoroughly with water and dried under high vacuum at 45° C. to give the desired product (0.027 g, 0.079 mmol, 39% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 11.22 (br. s., 1H), 8.63 (br. s., 1H), 7.93 (s, 1H), 7.89 (d, J=7.81 Hz, 1H), 7.62 (s, 1H), 7.58 (s, 1H), 7.47 (br. s., 1H), 2.43 (s, 3H), 1.29-1.38 (m, 2H), 0.95-1.04 (m, 2H); MS (ESI) m/z 334.2 [M+1]+.

Workup

  1. filtrationThe resulting mixture was filtered
  2. custompurified
  3. customreverse-phase preparatory HPLC (10-60% acetonitrile+0.1% TFA in water+0.1% TFA, over 30 min)
  4. additionFractions containing the desired product
  5. customremoved under reduced pressure
  6. filtrationSolids were collected by vacuum filtration
  7. washwashed thoroughly with water
  8. customdried under high vacuum at 45° C.

Sources & evidence

ORD record
ord-823257023454448f8fb6ca74c82cdee4
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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