Sodium Hydroxide → HCID 58456138、化合物

HRID 1040159ノート

反応式

HRID 1040159 の反応式
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:20]2[S:24][C:23]([C@@:25]3([OH:37])[CH2:30][CH2:29][C@H:28]([C:31]([O:33]C)=[O:32])[C:27]([CH3:36])([CH3:35])[CH2:26]3)=[N:22][CH:21]=2)[CH:6]=[C:7]([NH:9][C:10]2[N:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][N:11]=2)[CH:8]=1.[OH-].[Na+]>CO>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:20]2[S:24][C:23]([C@@:25]3([OH:37])[CH2:30][CH2:29][C@H:28]([C:31]([OH:33])=[O:32])[C:27]([CH3:35])([CH3:36])[CH2:26]3)=[N:22][CH:21]=2)[CH:6]=[C:7]([NH:9][C:10]2[N:15]=[C:14]([C:16]([F:18])([F:19])[F:17])[CH:13]=[CH:12][N:11]=2)[CH:8]=1

参加物

4

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 67432750HCID 67432750、化合物

生成物 1

HCID 58456138HCID 58456138、化合物収率 36.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A microwave vessel was charged with a solution of the compound of Step 3 (10 mg, 0.019 mmol) in MeOH, and sodium hydroxide (1.0 N in H2O, 56 μl, 0.056 mmol, 3 equiv) was added. The resultant cloudy orange suspension was irradiated in the microwave at 110° C. for 15 min. The reaction was not complete. Additional sodium hydroxide (1.0 N in H2O, 190 μL, 0.19 mmol, 10 eq) was added and the faintly yellow solution was irradiated at 150° C. for 30 min. The reaction mixture was concentrated in vacuo, then partitioned between diethyl ether (75 ml) and water (85 ml). The aqueous layer was acidified with 1N aqueous HCl to pH ˜3-4, then washed with EtOAc (2×35 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated, affording the title compound (3.6 mg, 35%) as an orange oil. MS ESI: [M+H]+ m/z 522.2 1H NMR (500 MHz, DMSO-d6) δ 10.5 (s, 1H), 8.85 (d, J=4.9 Hz, 1H), 8.24 (bs, 1H), 8.14 (s, 1H), 7.93 (s, 1H), 7.65 (s, 1H), 7.46 (s, 1H), 7.33 (d, J=4.9 Hz, 1H), 5.94 (bs, 1H), 4.03-3.99 (m, 3H), 3.14 (m, 2H), 2.19-2.16 (m, 2H), 1.86-1.83 (m, 2H), 1.66-1.60 (m, 2H), 1.17-1.11 (m, 6H). rhSYK activity=+++

後処理

  1. additionwas added
  2. customThe resultant cloudy orange suspension was irradiated in the microwave at 110° C. for 15 min
  3. customthe faintly yellow solution was irradiated at 150° C. for 30 min
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. custompartitioned between diethyl ether (75 ml) and water (85 ml)
  6. washwashed with EtOAc (2×35 ml)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-c65db116538f4cb18d7dd41051d39572
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

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