Potassium Hydroxide → (S)-pyrrolidine-2-carboxylic acid [4-methoxy-3-(3-pyrazin-2-yl-ureido)-phenyl]-amide

HRID 1821729노트

반응식

HRID 1821729 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2C(=O)C(F)(F)F)=[O:11])=[CH:5][C:4]=1[NH:23][C:24]([NH:26][C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1)=[O:25].[OH-].[K+]>CO.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C@@H:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)=[O:11])=[CH:5][C:4]=1[NH:23][C:24]([NH:26][C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1)=[O:25]

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 86587622(S)-1-(2,2,2-trifluoroethanoyl)-pyrrolidine-2-carboxylic acid [4-methoxy-3-(3-pyrazin-2-yl-ureido)-phenyl]-amide2회

생성물 1

HCID 67256377(S)-pyrrolidine-2-carboxylic acid [4-methoxy-3-(3-pyrazin-2-yl-ureido)-phenyl]-amide

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

A suspension of (S)-1-(2,2,2-trifluoro-ethanoyl)-pyrrolidine-2-carboxylic acid [4-methoxy-3-(3-pyrazin-2-yl-ureido)-phenyl]-amide (Compound 36, Example 6) (22 mg, 0.05 mmol) in a mixture of methanol (MeOH, 5 mL) and water (about 0.25 mL) was treated with KOH (100 mg, large excess). Within 10 minutes, all ingredients were in solution. The reaction mixture was treated with water (20 mL) and extracted with ethyl acetate (2×20 mL). The organic layers were combined and washed with water (10 mL) and brine (10 mL), dried with sodium sulfate, and concentrated to a tan solid (13 mg, 75%). 1H NMR (300 MHz, d6-DMSO) δ: 10.13 (s, 1H), 10.03 (s, 1H), 9.85 (s, 1H), 8.90 (s, 1H), 8.38-8.28 (m, 2H), 8.25 (d, J=2.6 Hz, 1H), 7.41 (dd, J=8.8, 2.6 Hz), 6.98 (d, J=8.8 Hz, 1H), 3.88 (s, 3H, 3.69 (dd, J=8.7, 5.6 Hz, 1H), 2.94-2.87 (m, 2H), 2.10-1.97 (m, 1H), 1.81-1.60 (m, 3H). LRMS (ESI, positive) m/e 357.1 (M+1).

후처리

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washwashed with water (10 mL) and brine (10 mL)
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated to a tan solid (13 mg, 75%)

출처 및 근거

ORD 기록
ord-855d31827d7a43738344db3851c9e152
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608618B2

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