Hydrochloric Acid → (R)-N-Hydroxy-4-{4-[4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-2H-pyridin-1-yl}-2-methanesulfonyl-2-methyl-butyramide hydrochloride

HRID 709291노트

반응식

HRID 709291 반응식
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][C@:23]([S:35]([CH3:38])(=[O:37])=[O:36])([CH3:34])[C:24]([NH:26][O:27]C4CCCCO4)=[O:25])[C:17](=[O:39])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[ClH:40].O1CCOCC1>C(Cl)Cl.CO>[ClH:40].[OH:27][NH:26][C:24](=[O:25])[C@@:23]([S:35]([CH3:38])(=[O:37])=[O:36])([CH3:34])[CH2:22][CH2:21][N:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([N:6]3[CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4][CH2:5]3)=[CH:14][CH:13]=2)=[CH:16][C:17]1=[O:39]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86671966HCID 86671966, 화합물

생성물 1

HCID 86671964(R)-N-Hydroxy-4-{4-[4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-2H-pyridin-1-yl}-2-methanesulfonyl-2-methyl-butyramide hydrochloride

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

(R)-4-{4-[4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-2H-pyridin-1-yl}-2-methanesulfonyl-2-methyl-N-(tetrahydro-pyran-2-yloxy)-butyramide (85.1 mg, 0.152 mmol) was dissolved in methylene chloride (5 mL) at ambient temperature. To this solution was added 4M HCl in 1,4-dioxane (0.304 mL, 1.22 mmol) and methanol (1 ml). The resulting solution was stirred at ambient temperature for 45 minutes. The solution was concentrated to a crude residue in vacuo. To the residue was added ethyl acetate (10 ml) and the resulting slurry was stirred overnight at ambient temperature. The slurry was filtered and washed with ethyl acetate/heptanes (1:1). The solid was dried in vacuo to afford (R)—N—Hydroxy-4-{4-[4-(4-hydroxymethyl-piperidin-1-yl)-phenyl]-2-oxo-2H-pyridin-1-yl}-2-methanesulfonyl-2-methyl-butyramide hydrochloride as an off-white solid. (72.7 mg). LCMS: M+1 478.6. 1H NMR (CD3OD, 400 MHZ) dppm, 7.82 (2H, d), 7.79 (1H, d), 6.84 (1H, d), 6.80-6.77 (1H, dd), 4.35-4.28 (1H, m), 4.00-3.93 (1H, m), 3.79-3.72 (4H, m), 3.55 (2H, d), 3.09 (3H, s), 2.64-2.56 (1H, m), 2.40-2.33 (1H, m), 2.16-2.13 (2H, d), 2.00-1.92 (1H, m), 1.87-1.76 (2H, m), 1.70 (3H, s).

후처리

  1. concentrationThe solution was concentrated to a crude residue in vacuo
  2. additionTo the residue was added ethyl acetate (10 ml)
  3. stirringthe resulting slurry was stirred overnight at ambient temperature
  4. filtrationThe slurry was filtered
  5. washwashed with ethyl acetate/heptanes (1:1)
  6. customThe solid was dried in vacuo

출처 및 근거

ORD 기록
ord-b6e10f07446f40f4997852ceb91bd69c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09180123B2

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