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(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid → HCID 178455449、化合物

HRID 82245
ノート
印刷プレビュー

反応式

HRID 82245 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:18]3[CH:17]=[N:16][CH:15]=[N:14][C:13]=3[N:12]([C:19]3([C:23]([CH3:31])([CH3:30])[O:24][SiH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][O:21][CH2:20]3)[CH:11]=2)=[O:9])[CH:5]=[N:6][CH:7]=1.[F:32][C:33]([F:45])([F:44])[C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41](O)=[O:42])=[CH:36][CH:35]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1.ClCCl.C(=O)(O)[O-].[Na+]>[C:26]([SiH2:25][O:24][C:23]([CH3:31])([CH3:30])[C:19]1([N:12]2[C:13]3[N:14]=[CH:15][N:16]=[CH:17][C:18]=3[C:10]([C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:41](=[O:42])[CH2:40][C:37]4[CH:36]=[CH:35][C:34]([C:33]([F:44])([F:32])[F:45])=[CH:39][CH:38]=4)[CH:7]=[N:6][CH:5]=3)=[O:9])=[CH:11]2)[CH2:20][O:21][CH2:22]1)([CH3:29])([CH3:28])[CH3:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178455448HCID 178455448、化合物

生成物 1

HCID 178455449HCID 178455449、化合物収率 92%

試薬・触媒・溶媒 3

HCID 1049
Pyridine
溶媒
HCID 6344Dichloromethane溶媒
HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
50 °C

実験手順

(5-Amino-pyridin-3-yl)-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}-methanone (Preparation 216, 30 mg, 0.068 mmol) was dissolved in dry pyridine (2 mL) under nitrogen and to this was added (4-trifluoromethyl-phenyl)-acetic acid (21 mg, 0.102 mmol), followed by HATU (39 mg, 0.102 mmol). The reaction mixture was heated to 50° C. and stirred overnight. The reaction was then cooled to room temperature, diluted with dichloromethane (5 mL) and saturated aqueous sodium bicarbonate was added (5 mL). The phases were separated and the aqueous layer was extracted with dichloromethane (3×5 mL). The combined organics were concentrated to dryness to afford N-(5-{7-[3-(tert-butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl}-pyridin-3-yl)-2-(4-trifluoromethyl-phenyl)-acetamide as a pale yellow solid 39 mg, 92% yield.

後処理

  1. temperatureThe reaction was then cooled to room temperature
  2. additionwas added (5 mL)
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (3×5 mL)
  5. concentrationThe combined organics were concentrated to dryness

出典と根拠

ORDレコード
ord-f3606333d59744beab7c49d3b5162430
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846698B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート