Water → HCID 178483042、化合物

HRID 1852874ノート

反応式

HRID 1852874 の反応式
Cl.[CH3:2][NH:3][CH3:4].C(=O)(O)[O-].[Na+].O.[Cl:11][C:12]1[N:17]=[C:16]([C:18]2[C:19](F)=[N:20][CH:21]=[C:22]([Cl:24])[CH:23]=2)[C:15]2[N:26]([CH2:38][C@H:39]3[CH2:44][CH2:43][C@H:42]([CH3:45])[CH2:41][CH2:40]3)[C:27]([N:29]3[CH2:34][CH2:33][O:32][C@@H:31]4[CH2:35][CH2:36][CH2:37][C@@H:30]34)=[N:28][C:14]=2[CH:13]=1>CCO>[Cl:24][C:22]1[CH:23]=[C:18]([C:16]2[C:15]3[N:26]([CH2:38][C@H:39]4[CH2:44][CH2:43][C@H:42]([CH3:45])[CH2:41][CH2:40]4)[C:27]([N:29]4[CH2:34][CH2:33][O:32][C@@H:31]5[CH2:35][CH2:36][CH2:37][C@@H:30]45)=[N:28][C:14]=3[CH:13]=[C:12]([Cl:11])[N:17]=2)[C:19]([N:3]([CH3:4])[CH3:2])=[N:20][CH:21]=1

参加物

6

反応物 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 516892Sodium BicarbonateHCID 178461232HCID 178461232、化合物

生成物 1

HCID 178483042HCID 178483042、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of dimethylamine hydrochloride (580 mg, 7.25 mmol) and sodium bicarbonate (812 mg, 9.67 mmol) in EtOH:water (4 mL:2 mL) was added 6-chloro-4-(5-chloro-2-fluoropyridin-3-yl)-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine (racemic) (125 mg, 0.24 mmol). The reaction was heated to 90° C. for 5 hours. The reaction was then concentrated and diluted with EtOAc. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification of the residue on a silica gel column (0 to 45% EtOAc/hexanes) afforded 5-chloro-3-{6-chloro-2-[(trans)-hexahydrocyclopenta[b][1,4]oxazin-4(4aH)-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridin-4-yl}-N,N-dimethylpyridin-2-amine (racemic). MS ES calc'd. for C28H36Cl2N6O [M+H]+ 543. found 543.

後処理

  1. concentrationThe reaction was then concentrated
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue on a silica gel column (0 to 45% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-6acb84cb02bd4df8ac78b0ac2188e5ab
出典データセット
uspto-grants-2015_02
特許番号
US08962611B2

反応ノート

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