Hydrochloric Acid → HCID 68109119, compound

HRID 2179420Notes

Reaction equation

HRID 2179420 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH:11]([CH2:15][F:16])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:3]=1.Cl>CO>[ClH:1].[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH:11]([CH2:15][F:16])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:18])=[O:19])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68109120HCID 68109120, compound

Product 1

HCID 68109119HCID 68109119, compoundYield 144.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of step D (8 mg, 0.02 mmol) was converted to the hydrochloride salt by dissolving in methanol and treating with 1.25 M HCl in methanol. The reaction was concentrated in vacuo to afford 6-chloro-1-(fluoromethyl)-8-(phenyl sulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (6 mg, 71%, AUC HPLC 96%) as a white solid: mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 9.51 (br s, 2H), 8.49 (d, J=1.6 Hz, 1H), 8.08-8.04 (m, 3H), 7.73-7.62 (m, 3H), 6.52-6.40 (m, 1H), 4.02-3.95 (m, 1H), 3.71-3.34 (m, 5H); APCI MS m/z 402 [M+Na]+.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-f27762a0b6734b78b8d3c846486840b0
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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