Potassium Phosphate, Tribasic → HCID 67125562, compound
Reaction equation
Cl[C:2]1[N:7]=[C:6]2[S:8][C:9]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([NH:20][C:21](=[O:33])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=4)[CH:17]=[CH:16][C:15]=3[CH3:34])=[O:12])=[CH:10][C:5]2=[N:4][CH:3]=1.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37](B(O)O)[CH:36]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>>[C:31]([C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([NH:20][C:18]1[CH:17]=[CH:16][C:15]([CH3:34])=[C:14]([NH:13][C:11]([C:9]2[S:8][C:6]3=[N:7][C:2]([C:37]4[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=4)=[CH:3][N:4]=[C:5]3[CH:10]=2)=[O:12])[CH:19]=1)=[O:33])([CH3:30])[CH3:29])#[N:32]Participants
Reactant 4
Product 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 3-chloro-N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)thieno[2,3-b]pyrazine-6-carboxamide 95 (204 mmol, 100 mg), pyridine-3-boronic acid (0.306 mmol, 37 mg), potassium phosphate, tribasic (0.408, 87 mg), (0.05 eq, 9 mg), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.1 eq, 9 mg) was stirred at 100° C. for 30 min. Evaporated to dryness and purified by chromatography (0-100% ethyl acetate in CH2Cl2) and HPLC to yield N-(5-(3-(2-cyanopropan-2-yl)benzamido)-2-methylphenyl)-3-(pyridin-3-yl)thieno[2,3-b]pyrazine-6-carboxamide 96j (3 mg, 2%). NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 2.29 (s, 3H), 7.32 (d, J=8.2 Hz, 1H), 7.62 (m, 3H), 7.76 (d, J=7.8 Hz, 1H), 7.90 (s, 1H), 7.96 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 8.59 (s, 1H), 8.64 (m, 1H), 8.75 (m, 1H), 9.45 (s, 1H), 9.58 (s, 1H), 10.38 (s, 1H), 10.54 (s, 1H). (m/z)=534 (M+H)+.
Workup
- customEvaporated to dryness
- custompurified by chromatography (0-100% ethyl acetate in CH2Cl2) and HPLC
Sources & evidence
- ORD record
- ord-52d995e86f8440bb9f902ce14f0bd5ed
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08669256B2
Reaction notes
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