Hydrochloric Acid → HCID 18406947, compound

HRID 1016421Notes

Reaction equation

HRID 1016421 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([CH2:17][O:18][C:19]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[F:34])=[C:26]4[N:21]([C:22]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[F:41])=[N:23][N:24]=[CH:25]4)[N:20]=3)[N:16]=[C:10]2[CH2:9]1)=O)(C)(C)C.[ClH:42]>C(OCC)(=O)C>[ClH:42].[F:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:27]1[C:19]([O:18][CH2:17][C:15]2[N:16]=[C:10]3[CH2:9][NH:8][CH2:13][CH2:12][N:11]3[N:14]=2)=[N:20][N:21]2[C:26]=1[CH:25]=[N:24][N:23]=[C:22]2[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[F:41]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69363038HCID 69363038, compound

Product 1

HCID 18406947HCID 18406947, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To 2-[3,7-bis(2-Fluorophenyl)pyrazolo[1,5-d][1,2,4]triazin-2-yloxymethyl]-5,6-dihydro-8H-[1,2,4]triazolo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (100 mg, 0.18 mmol) in ethyl acetate (3 ml) was added a saturated solution of hydrogen chloride in: ethyl acetate (2 ml), and the resultant mixture was stirred at room temperature for 5.5 h. 2-[3,7-Bis(2-fluorophenyl)pyrazolo[1,5-d][1,2,4]triazin-2-yloxymethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine hydrochloride was precipitated as a pale yellow solid, and was separated by filtration, washed thoroughly with ethyl acetate and dried (71 mg). Data for the title compound: 1H NMR (360 MHz, DMSO) δ 3.67 (2H, m), 4.37 (2H, t, J=5.8 Hz), 4.48 (2H, s), 5.39 (2H, s), 7.33-7.55 (5H, m), 7.69 (1H, td, J=7.6, 1.7 Hz), 7.77 (1H, m), 7.92 (1H, td, J=7.3, 1.7 Hz), 9.44 (1H, s), 10.07 (2H, br s); MS (ES+) m/e 461 [MH]+.

Workup

  1. custom2-[3,7-Bis(2-fluorophenyl)pyrazolo[1,5-d][1,2,4]triazin-2-yloxymethyl]-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine hydrochloride was precipitated as a pale yellow solid
  2. customwas separated by filtration
  3. washwashed thoroughly with ethyl acetate
  4. customdried (71 mg)

Sources & evidence

ORD record
ord-4401ebecb57445ba8ba10f335db6c5aa
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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