Hydrochloric Acid → HCID 178479423, compound

HRID 452307Notes

Reaction equation

HRID 452307 reaction equation
C(O[N:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][F:23])=[C:15]([Br:24])[CH:14]=1)[C:7]([N:9]=C=O)=[NH:8])(C)(C)C.[ClH:25]>O1CCOCC1.O.C(#N)C>[ClH:25].[Br:24][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[O:19][CH2:20][CH2:21][CH2:22][F:23])[CH2:12][NH:6][C:7]([NH2:9])=[NH:8]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86709249HCID 86709249, compound

Product 1

HCID 178479423HCID 178479423, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1,3-bis(tert-butoxy-carbonyl-[3-bromo-4-(3-fluoro-propoxy)-benzyl]-guanidine (250.6 mg, 50 mmol) in 4N HCl in dioxane (6 mL) was heated to 50° C. for 2 h. The reaction mixture was diluted with water (4 mL) and ACN (1 mL) and lyophilized to afford N-[3-bromo-4-(3-fluoro-propoxy)-benzyl]-guanidine hydrochloride as a white solid (169.1 mg, 99% yield). 1H NMR (DMSO-d6, 600 MHz): δ 8.03 (br t, 1H), 7.55 (m, 1H), 7.31-7.27 (m, 2H), 7.15 (d, J=9 Hz, 1H), 4.72 (t, J=6 Hz, 1H), 4.56 (t, J=6 Hz, 1H), 4.30 (m, 2H), 4.15 (t, J=6 Hz, 2H), 2.19-2.06 (m, 2h).

Sources & evidence

ORD record
ord-91d29ffe972241fbbf052cc9f19f1a9c
Source dataset
uspto-grants-2013_07
Patent number
US08491868B2

Reaction notes

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