Hydrochloric Acid → HCID 67436165, compound

HRID 521369Notes

Reaction equation

C(OC([NH:8][CH:9]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:10]1[N:14]2[CH2:15][CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][C:13]2=[N:12][N:11]=1)=O)(C)(C)C.CO.[ClH:35]>>[ClH:32].[ClH:35].[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:9]([C:10]2[N:14]3[CH2:15][CH2:16][NH:17][CH2:18][C:13]3=[N:12][N:11]=2)[NH2:8])=[CH:27][CH:28]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 67438472HCID 67438472, compound

Product 1

HCID 67436165HCID 67436165, compoundYield 99%

Procedure

A solution of tert-butyl 3-((tert-butoxycarbonylamino)(4-chlorophenyl)methyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate (0.652 g, 1.41 mmol) in MeOH (7.03 mL, 1.41 mmol) was saturated with HCl (g). The reaction mixture was stirred at room temperature for 30 minutes and then concentrated in vacuo to afford (4-chlorophenyl)(5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)methanamine bishydrochloride as a foam (0.47 g, 99%). LCMS (APCI+) M+H+: 264 (50%), 266 (10%), 267 (3%); rt=1.76 minutes. 1H NMR (400 MHz, d6-DMSO) δ □10.62 (s, 1H), 10.18 (s, 1H), 9.43 (s, 3H), 7.57 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.6 Hz, 2H), 6.13 (m, 1H), 4.51 (m, 2H), 4.44 (m, 1H), 3.56 (m, 3H).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-563ba7dbe26c492685bb731954afc397
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328091B2

Reaction notes

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