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

HRID 2060645Notes

Reaction equation

HRID 2060645 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][C:8]=2[F:17])=[N:4][C:3]=1[C:18]([NH2:20])=[O:19].Cl[C:22]1[N:27]=[C:26]([CH3:28])[C:25]([C:29]([OH:32])([CH3:31])[CH3:30])=[CH:24][CH:23]=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]>[F:17][C:8]1[CH:9]=[C:10]([C:13]([OH:16])([CH3:15])[CH3:14])[CH:11]=[CH:12][C:7]=1[C:5]1[S:6][C:2]([NH:1][C:22]2[CH:23]=[CH:24][C:25]([C:29]([OH:32])([CH3:30])[CH3:31])=[C:26]([CH3:28])[N:27]=2)=[C:3]([C:18]([NH2:20])=[O:19])[N:4]=1

Participants

7

Reactant 5

HCID 64052-Methyl-2-butanolHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 583352575-Amino-2-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamideHCID 583352662-(6-Chloro-2-methylpyridin-3-yl)propan-2-ol

Product 1

HCID 446231762-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-5-{[5-(1-hydroxy-1-methylethyl)-6-methylpyridin-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-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide (Example 25, Step 4) (150 mg, 0.51 mmol), 2-(6-chloro-2-methylpyridin-3-yl)propan-2-ol (Example 13, Step 1) (94 mg, 0.51 mmol), Pd2(dba)3 (47 mg, 0.051 mmol), X-PHOS (121 mg, 0.25 mmol), potassium carbonate (70 mg, 0.51 mmol), and tert-amyl alcohol (1.0 mL) as starting materials. 1H NMR. (500 MHz, d6-DMSO): δ 11.15 (s, 1H), 8.27 (t, 1H), 7.82 (s, 1H), 7.74 (d, 1H), 7.62 (s, 1H), 7.40 (m, 2H), 6.97 (d, 1H), 5.25 (s, 1H), 5.02 (s, 1H), 2.73 (s, 3H), 1.49 (s, 6H), 1.44 (s, 6H). LRMS (APCI) calc'd for C22H26FN4O3S [M+H]+ 455.2, found 455.0.

Sources & evidence

ORD record
ord-df3d124f78e64b81bea511ed1612ceaa
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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