Hydrochloric Acid → HCID 68108805, compound

HRID 2179388Notes

Reaction equation

HRID 2179388 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:10]2[O:11][C:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:13]=3[C:9]=2[CH:8]=[C:7]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH:6]=1)=[O:4].[ClH:34]>O1CCCC1>[ClH:34].[CH3:1][NH:2][C:3]([C:5]1[C:10]2[O:11][C:12]3[CH2:17][CH2:16][NH:15][CH2:14][C:13]=3[C:9]=2[CH:8]=[C:7]([S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:26])=[O:27])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68109753HCID 68109753, compound

Product 1

HCID 68108805HCID 68108805, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from step B (41 mg, 0.08 mmol) in tetrahydrofuran (2.5 mL) was added concentrated HCl (0.5 mL) at 0° C. The reaction mixture was slowly allowed to reach to ambient temperature. After stirring overnight at ambient temperature the precipitate was filtered, washed with tetrahydrofuran, and dried overnight in vacuo at 45° C. to give N-methyl-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine-6-carboxamide hydrochloride (21 mg, 59%, AUC HPLC>99%) as a white solid: mp <<MP data>>; 1H NMR (DMSO-d6, 400 MHz) δ 9.35 (br s, 2H), 8.56-8.47 (m, 2H), 8.14 (d, J=2.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.72-7.58 (m, 3H), 4.41 (s, 2H), 3.54 (t, J=6.0 Hz, 2H), 3.14 (t, J=6.0 Hz, 2H), 2.86 (d, J=4.8 Hz, 3H); APCI MS m/z 371 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-6fd551bf4cc34ce1bdbaf82a080fa6db
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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