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Water → 2-(6-(1H-pyrazol-5-yl)-2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one

HRID 885964
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HRID 885964 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[CH2:14]C(C)(C)N[C:17](=O)[C:18]=4[N:19]=3)[C:6]=2[CH:23]=1.[NH:24]1[CH:28]=[CH:27][C:26](B(O)O)=[N:25]1.C([O-])([O-])=O.[Na+].[Na+].[OH2:38]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:5][C:6]1([CH3:23])[NH:7][C:14](=[O:38])[C:13]2[S:12][C:11]([N:7]3[C:6]4[CH:23]=[C:2]([C:26]5[NH:25][N:24]=[CH:28][CH:27]=5)[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)=[N:19][C:18]=2[CH2:17]1
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참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 685972362-(6-Bromo-2,3-dihydrobenzo[1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydro-[1,3]thiazolo[5,4-d]pyridin-4(5h)-oneHCID 178514837HCID 178514837, 화합물

생성물 1

HCID 445779212-(6-(1H-pyrazol-5-yl)-2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-6,6-dimethyl-6,7-dihydrothiazolo[5,4-c]pyridin-4(5H)-one수율 60%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

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온도
140 °C

실험 절차

A stirred suspension of Example 39 (0.050 g, 0.14 mmol), 3-pyrazoleboronic acid (0.055 g, 0.42 mmol), Na2CO3 (0.045 g, 0.42 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.005 g) in a mixture of DME (4 mL) and water (1 mL) was heated to 140° C. in a sealed tube, under microwave irradiation, for 30 minutes. After cooling to r.t., the reaction mixture was concentrated in vacuo. Purification by preparative HPLC (Method 7) gave the title compound (0.0318 g, 60%) as an off-white solid. δH (CDCl3/CD3OD) 8.20 (1H, s), 7.60 (1H, s), 7.40 (1H, dd, J 8.7 and J 2.1 Hz), 7.00 (1H, d, J 8.5 Hz), 6.50 (1H, s), 4.40 (2H, m), 4.10 (2H, m), 2.90 (2H, s), 1.40 (6H, s). LCMS (ES+) 381.0 (M)+, RT 2.85 minutes (Method 2).

후처리

  1. temperatureAfter cooling to r.t.
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customPurification by preparative HPLC (Method 7)

출처 및 근거

ORD 기록
ord-132896515c86457a8f0bc7a91b4e90d3
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242116B2

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