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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
Notes
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Reaction equation

HRID 885964 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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, compound

Product 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)-one
Yield 60%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
140 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-132896515c86457a8f0bc7a91b4e90d3
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08242116B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes