(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid → HCID 178455449, 화합물

HRID 82245

반응식

HRID 82245 반응식
[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]

참가 물질

7

반응물 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, 화합물

생성물 1

HCID 178455449HCID 178455449, 화합물수율 92%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
50 °C

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-f3606333d59744beab7c49d3b5162430
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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