2-Methyl-2-butanol → 2-[4-(1-Hydroxy-1-methylethyl)phenyl]-5-{[5-(methylsulfonyl)pyridin-2-yl]amino}-1,3-thiazole-4-carboxamide
Reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([OH:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:17]([NH2:19])=[O:18].Br[C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][N:22]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C(=O)([O-])[O-].[K+].[K+].C(O)(CC)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:16][C:13]([C:10]1[CH:9]=[CH:8][C:7]([C:5]2[S:6][C:2]([NH:1][C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][N:22]=3)=[C:3]([C:17]([NH2:19])=[O:18])[N:4]=2)=[CH:12][CH:11]=1)([CH3:15])[CH3:14]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared as described in Example 1, Step 2 using 5-amino-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide (Example 5, Step 3) (150 mg, 0.54 mmol), 2-bromo-5-(methylsulfonyl)pyridine (128 mg, 0.54 mmol), Pd2(dba)3 (30 mg, 0.032 mmol), X-PHOS (77 mg, 0.16 mmol), potassium carbonate (75 mg, 0.54 mmol), and tert-amyl alcohol (1.1 ml) as starting materials. 1H NMR (500 MHz, d6-DMSO) δ 11.72 (s, 1H), 8.79 (d, 1H), 8.13 (dd, 1H), 7.91 (m, 3H), 7.79 (s, 1H), 7.57 (d, 2H), 7.44 (d, 1H), 5.74 (s, 1H), 3.26 (s, 3H), 1.44 (s, 6H). LRMS (APCI) calcd for C19H21N4O4S2 [M+H]+ 433.1, found 433.0.
Sources & evidence
- ORD record
- ord-1d205228d42d4607b7d7215a2a97ae17
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278335B2
Reaction notes
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