Hydrochloric Acid → HCID 68109416, compound

HRID 2179386Notes

Reaction equation

HRID 2179386 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([C:30]3[CH:31]=[N:32][NH:33][CH:34]=3)[C:13]3[O:22][C:21]4[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[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:35]>O1CCCC1>[ClH:35].[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([C:30]3[CH:34]=[N:33][NH:32][CH:31]=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:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68109761HCID 68109761, compound

Product 1

HCID 68109416HCID 68109416, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from step A (36 mg, 0.07 mmol) in tetrahydrofuran (2.5 mL) was added concentrated HCl (0.5 mL) at 0° C. The reaction mixture was slowly allowed to reach ambient temperature and stirred overnight. The precipitate was filtered, washed with tetrahydrofuran, and dried overnight in vacuo at 45° C. to give 8-(phenylsulfonyl)-6-(1H-pyrazol-4-yl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (18 mg, 58%, AUC HPLC>99%) as a white solid: mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 9.46 (br s, 2H), 8.42 (s, 2H), 8.19 (d, J=1.6 Hz, 1H), 8.16 (d, J=2.0 Hz, 1H), 8.08-8.01 (m, 2H), 7.71-7.57 (m, 3H), 4.41 (s, 2H), 3.64 (br s, 2H); 3.22-3.12 (m, 2H); APCI MS m/z 380 [M+H]+.

Workup

  1. customto reach ambient temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with tetrahydrofuran
  4. customdried overnight in vacuo at 45° C.

Sources & evidence

ORD record
ord-3e8ee8dace8b4044835b6e7289a88bb3
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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