Methylcarbamoyl chloride → (6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl methylcarbamate

HRID 588156

反応式

HRID 588156 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[CH:3]=1.[CH3:34][NH:35][C:36](Cl)=[O:37].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:34][NH:35][C:36](=[O:37])[O:9][CH2:8][C:6]1[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:4]=2[CH:3]=[C:2]([Cl:1])[N:7]=1

参加物

5

反応物 3

HCID 80931Methylcarbamoyl chlorideHCID 81531DiisopropylethylamineHCID 118271763(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol2 回

生成物 1

HCID 118272304(6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl methylcarbamate収率 76.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
35 °C

実験手順

A solution of (6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methanol (Intermediate 35B, 200 mg, 0.439 mmol) and methylaminoformyl chloride (45.1 mg, 0.483 mmol) in DCM (1462 μl) was treated with DIEA (153 μl, 0.877 mmol) and stirred @ 35° C. for 1 h Reaction was dilluted in with DCM and concentrated in vacuo on silica. Material was purified by normal phase column chromotography eluting with Hex/EtOAc (0-40%) affording (6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl methylcarbamate (172 mg, 0.335 mmol, 76% yield) as a white solid. MS: [M+H]+ m/z 513.

後処理

  1. customReaction
  2. concentrationconcentrated in vacuo on silica
  3. customMaterial was purified by normal phase column chromotography
  4. washeluting with Hex/EtOAc (0-40%)

出典と根拠

ORDレコード
ord-7e22731b8e114406993c3d8de19fee65
出典データセット
uspto-grants-2016_01
特許番号
US09226922B2

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