Hydrochloric Acid → HCID 178484512, compound

HRID 526746Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][N:14]([CH3:21])[CH2:15][CH:16](OC)[O:17]C)=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.[ClH:22]>>[ClH:22].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][N:14]([CH3:21])[CH2:15][CH:16]=[O:17])=[CH:11][NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 178495915HCID 178495915, compound

Product 1

HCID 178484512HCID 178484512, compound

Procedure

A solution of N-((3-(4-fluorophenyl)-1H-pyrazol-4-yl)methyl)-2,2-dimethoxy-N-methylethanamine (3.92 g, 13.36 mmol, 1.00 equiv) in 6N hydrochloric acid (40 mL) was stirred at 80° C. for 2 h. The resulting mixture was concentrated under vacuum to yield 3.82 g of crude 2-(((3-(4-fluorophenyl)-1H-pyrazol-4-yl)methyl)(methyl)amino)acetaldehyde hydrochloride as a yellow solid. 1H NMR (300 MHz, DMSO) δ: 9.43 (s, 1H), 8.07 (s, 1H), 7.73-7.52 (m, 2H), 7.41-7.21 (m, 2H), 4.54-4.25 (m, 2H), 4.12-4.00 (m, 2H), 2.55 (s, 3H) ppm. LCMS (method C, ESI): RT=0.59 min, m/z=266.0 [M+H+H2O]+.

Workup

concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-8201c982aeb94651be24cc755102ce69
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346761B2

Reaction notes

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