2-Methyl-2-butanol → 5-{[5-(1-Hydroxy-1-methylethyl)-6-methylpyridin-2-yl]amino}-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide

HRID 2060618Notes

Reaction equation

HRID 2060618 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].Cl[C:21]1[N:26]=[C:25]([CH3:27])[C:24]([C:28]([OH:31])([CH3:30])[CH3:29])=[CH:23][CH: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:31][C:28]([C:24]1[CH:23]=[CH:22][C:21]([NH:1][C:2]2[S:6][C:5]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([OH:16])([CH3:15])[CH3:14])=[CH:11][CH:12]=3)=[N:4][C:3]=2[C:17]([NH2:19])=[O:18])=[N:26][C:25]=1[CH3:27])([CH3:30])[CH3:29]

Participants

7

Reactant 5

HCID 64052-Methyl-2-butanolHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 583352645-Amino-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamideHCID 583352662-(6-Chloro-2-methylpyridin-3-yl)propan-2-ol

Product 1

HCID 574828035-{[5-(1-Hydroxy-1-methylethyl)-6-methylpyridin-2-yl]amino}-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

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-(6-chloro-2-methylpyridin-3-yl)propan-2-ol (100 mg, 0.54 mmol), Pd2(dba)3 (30 mg, 0.032 mmol), X-PHOS (77 mg, 0.16 mmol), potassium carbonate (82 mg, 0.60 mmol), and tert-amyl alcohol (1.1 ml) as starting materials. 1H NMR (500 MHz, d6-DMSO) δ 11.17 (s, 1H), 7.87 (d, 2H), 7.34 (d, 1H), 7.69 (s, 1H), 7.58 (s, 1H), 7.55 (d, 2H), 6.95 (d, 1H), 5.11 (s, 1H), 5.02 (s, 1H), 2.76 (s, 3H), 1.49 (s, 6H), 1.44 (s, 6H). LRMS (APCI) calc'd for C22H27N4O3S [M+H]+ 427.2, found 427.0.

Sources & evidence

ORD record
ord-21fe9570b4ef4f8282454986eb62990b
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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