Ammonium Chloride → N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(2-methoxyethoxy)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide

HRID 1621956

反応式

HRID 1621956 の反応式
F[C:2]1[C:7]([C:8]2[N:13]=[C:12]([CH3:14])[N:11]=[C:10]([NH2:15])[N:9]=2)=[CH:6][C:5]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[CH:4][N:3]=1.[NH2:21][C:22]1[CH:23]=[C:24]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:25]([Cl:28])=[N:26][CH:27]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[NH4+].[Cl-]>CN(C=O)C>[NH2:15][C:10]1[N:11]=[C:12]([CH3:14])[N:13]=[C:8]([C:7]2[C:2]([NH:21][C:22]3[CH:23]=[C:24]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[C:25]([Cl:28])=[N:26][CH:27]=3)=[N:3][CH:4]=[C:5]([O:16][CH2:17][CH2:18][O:19][CH3:20])[CH:6]=2)[N:9]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amide2 回HCID 66612001HCID 66612001、化合物HCID 71480920N-(5-amino-2-chloro-3-pyridinyl)methanesulfonamide

生成物 1

HCID 59548407N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(2-methoxyethoxy)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide収率 66.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a stirred mixture of 4-(2-fluoro-5-(2-methoxyethoxy)pyridin-3-yl)-6-methyl-1,3,5-triazin-2-amine (0.105 g, 0.376 mmol) and N-(5-amino-2-chloropyridin-3-yl)methanesulfonamide (Example 330 step 2, 0.0977 g, 0.441 mmol) in DMF (1 mL) in 5 mL microwave vial, NaHMDS (Aldrich, 1 M in THF, 1.20 mL, 1.20 mmol) was added slowly at 0° C. The dark brown mixture was stirred at 0° C. for 30 min. Additional NaHMDS (0.5 mL) was added at 0° C. and the stirring was continued at 0° C. for 30 min. The reaction mixture was poured into 30 mL of sat'd NH4Cl and stirred for 30 min. The resulting yellow solid was collected via filtration and washed with copious amount of water and air-dried to afford N-(5-(3-(4-amino-6-methyl-1,3,5-triazin-2-yl)-5-(2-methoxyethoxy)pyridin-2-ylamino)-2-chloropyridin-3-yl)methanesulfonamide (0.120 g, 66% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.96 (s, 1H) 9.62 (s, 1H) 8.61 (d, J=19.95 Hz, 2H) 8.44 (d, J=2.74Hz, 1H) 8.21 (d, J=2.54 Hz, 1H) 7.75-8.01 (m, 2H) 4.12-4.27 (m, 2H) 3.69 (d, J=4.30 Hz, 2H) 3.33 (br. s., 3H) 3.13 (s, 3H) 2.45 (s, 3H). m/z (ESI, positive ion): 481.0 (M+H)+.

後処理

  1. additionwas added slowly at 0° C
  2. waitthe stirring was continued at 0° C. for 30 min
  3. stirringstirred for 30 min
  4. filtrationThe resulting yellow solid was collected via filtration
  5. washwashed with copious amount of water
  6. customair-dried

出典と根拠

ORDレコード
ord-7b59c2e1d3aa4317a47b59f7e4faaa01
出典データセット
uspto-grants-2014_07
特許番号
US08772480B2

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