Hydrochloric Acid → HCID 68109300, compound

HRID 2179385Notes

Reaction equation

HRID 2179385 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)[C:13]3[O:22][C:21]4[CH2:20][CH2:19][NH:18][CH2:17][C:16]=4[C:14]=3[CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:28]>ClCCl.CO>[ClH:28].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([N:23]3[CH:27]=[CH:26][CH:25]=[N:24]3)[C:13]3[O:22][C:21]4[CH2:20][CH2:19][NH:18][CH2:17][C:16]=4[C:14]=3[CH:15]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68108369HCID 68108369, compound

Product 1

HCID 68109300HCID 68109300, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The product obtained in step C (23 mg, 0.06 mmol) was converted to the hydrochloride salt by dissolving in dichloromethane and treating with 1.25 M HCl in methanol. The reaction mixture was concentrated in vacuo to give 8-(phenylsulfonyl)-6-(1H-pyrazol-1-yl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (24 mg, 96%, AUC HPLC 98.6%) as a white solid: mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 9.35 (br s, 2H), 8.69-8.65 (m, 1H), 8.36 (d, J=2.0 Hz, 1H), 8.30 (d, J=1.6 Hz, 1H), 8.05-7.99 (m, 2H), 7.92 (d, J=1.6 Hz, 1H), 7.74-7.59 (m, 3H), 6.89 (d, J=2.0 Hz, 1H), 4.43 (s, 2H), 3.55 (t, J=6.0 Hz, 2H), 3.17 (t, J=6.0 Hz, 2H); ESI MS m/z 380 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-cd3e99e707084946b53231fbf6fb9be6
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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