Sodium Hydroxide → 1-{5-[({5-[(3,4-Difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}-4-methylpiperidine-4-carboxylic acid

HRID 1713778ノート

反応式

HRID 1713778 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:14][C:13]([C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:29][CH2:28][C:27]([CH3:34])([C:30]([O:32]C)=[O:31])[CH2:26][CH2:25]4)=[N:22][CH:23]=3)=[O:16])=[N:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[O:14][C:13]([C:15]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:25][CH2:26][C:27]([CH3:34])([C:30]([OH:32])=[O:31])[CH2:28][CH2:29]4)=[N:22][CH:23]=3)=[O:16])=[N:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 59464069Methyl 1-{5-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}-4-methylpiperidine-4-carboxylate

生成物 1

HCID 594640331-{5-[({5-[(3,4-Difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}-4-methylpiperidine-4-carboxylic acid収率 84%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 1-{5-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}-4-methylpiperidine-4-carboxylate (Example 631; 282 mg, 0.60 mmol) in MeOH (10 mL) was added a 2M solution of NaOH (1.5 mL). The resulting yellow solution was allowed to stir at ambient temperature overnight. The reaction mixture was then heated to 50° C. for 8 hours and allowed to stir at ambient temperature overnight. The volatile organics were removed by evaporation, the aqueous residue was washed with ether (50 mL) and aqueous phase adjusted to pH ˜1 with 2M HCl. The resultant suspension was filtered and dried under vacuum at ambient temperature to give the title compound (230 mg, 0.502 mmol, 84%); 1H NMR δ 1.21 (s, 3H), 1.47-1.54 (m, 2H), 2.03-2.08 (m, 2H), 3.29-3.36 (m, 2H), 3.95-4.00 (m, 2H), 7.30 (d, 1H), 7.37-7.41 (m, 1H), 7.48 (q, 1H), 7.69-7.75 (m, 1H), 8.15 (d, 1H), 8.54 (s, 1H), 11.25 (s, 1H), 11.37 (s, 1H); CO2H not seen; MS m/e MH+ 459.

後処理

  1. temperatureThe reaction mixture was then heated to 50° C. for 8 hours
  2. stirringto stir at ambient temperature overnight
  3. customThe volatile organics were removed by evaporation
  4. washthe aqueous residue was washed with ether (50 mL) and aqueous phase
  5. filtrationThe resultant suspension was filtered
  6. customdried under vacuum at ambient temperature

出典と根拠

ORDレコード
ord-ca98590b0f8e42ac9872e3fb0fa4bbe1
出典データセット
uspto-grants-2010_09
特許番号
US07795283B2

反応ノート

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