Sodium Hydroxide → HCID 136333947, compound
Reaction equation
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH:12]3[CH:21]4[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]4)[CH2:15][CH2:14][N:13]3C(OC(C)(C)C)=O)=[N:5][C:4]=2[CH:3]=1.[NH2:29][C:30]1[CH:34]=C(Br)S[C:31]=1[C:36]([NH2:38])=O.C(OC(N1CC2CC1(C(O)=O)C2)=O)(C)(C)C.C([Cl:62])(=O)OCC(C)C.[OH-].[Na+]>CO.O1CCCC1.C(N(CC)CC)C>[ClH:62].[CH:12]1([C:6]2[NH:7][C:8](=[O:11])[C:9]3[S:10][C:2]([C:31]4[CH:36]=[N:38][NH:29][C:30]=4[CH3:34])=[CH:3][C:4]=3[N:5]=2)[CH:21]2[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14][NH:13]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
In the same manner as in Example 71, step A, tert-butyl 1-(6-bromo-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)octahydroisoquinoline-2(1H)-carboxylate (180 mg) as a colorless solid from 3-amino-5-bromothiophene-2-carboxamide (0.22 g) produced in Example 1, step D, 2-(tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid (0.57 g), 2-methylpropyl chlorocarbonate (0.27 g), triethylamine (0.20 g) and tetrahydrofuran (10 mL), and 2M aqueous sodium hydroxide solution (1 mL) and methanol (5 mL). In the same manner as in Example 83, step C, 2-(decahydroisoquinolin-1-yl)-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one hydrochloride was obtained from the compound obtained above, tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (270 mg), cesium carbonate (290 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane complex (1:1)(18 mg), 1,2-dimethoxyethane (10 mL), water (1 mL), and 4M hydrochloric acid/ethyl acetate solution (2 mL) and methanol (10 mL). This was purified by basic silica gel column chromatography (methanol/ethyl acetate) to give the title compound (36 mg) as a colorless solid.
Sources & evidence
- ORD record
- ord-56e1a134953c400b90a1a9d2d536f96d
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933069B2
Reaction notes
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