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

HRID 2060617Notes

Reaction equation

HRID 2060617 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[N:26]=[CH:25][C:24]([C:27]([OH:30])([CH3:29])[CH3:28])=[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: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:22]=[CH:23][C:24]([C:27]([OH:30])([CH3:29])[CH3:28])=[CH:25][N:26]=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

HCID 64052-Methyl-2-butanolHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 223919732-(6-Bromo-3-pyridyl)-2-propanolHCID 583352645-Amino-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide

Product 1

HCID 446230422-[4-(1-Hydroxy-1-methylethyl)phenyl]-5-{[5-(1-hydroxy-1-methylethyl)pyridin-2-yl]amino}-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-bromopyridin-3-yl)propan-2-ol (for preparation, see WO 2004/050024 A2 Example 120 Step A) (117 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 (1.2 ml) as starting materials. 1H NMR (500 MHz, d6-DMSO) δ 11.25 (s, 1H), 8.42 (d, 1H), 7.88 (d, 2H), 7.82 (dd, 1H), 7.72 (s, 1H), 7.61 (s, 1H), 7.55 (d, 2H), 7.14 (d, 1H), 5.13 (s, 1H), 5.11 (s, 1H), 1.44 (s, 6H), 1.43 (s, 6H). LRMS (APCI) calc'd for C21H25N4O3S [M+H]+ 413.2, found 413.0.

Sources & evidence

ORD record
ord-773b42171a8a4bb18d09f018882cdae5
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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