2-Methyl-2-butanol → 5-{[5-(1-Hydroxy-1-methylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

HRID 2060639Notes

Reaction equation

HRID 2060639 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:19]([NH2:21])=[O:20].Br[C:23]1[N:28]=[CH:27][C:26]([C:29]([OH:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=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:32][C:29]([C:26]1[CH:25]=[CH:24][C:23]([NH:1][C:2]2[S:6][C:5]([C:7]3[CH:8]=[N:9][C:10]([N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[CH:11][CH:12]=3)=[N:4][C:3]=2[C:19]([NH2:21])=[O:20])=[N:28][CH:27]=1)([CH3:31])[CH3:30]

Participants

7

Reactant 5

HCID 64052-Methyl-2-butanolHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 223919732-(6-Bromo-3-pyridyl)-2-propanolHCID 583352605-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

Product 1

HCID 446231055-{[5-(1-Hydroxy-1-methylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The title compound was prepared as described in Example 22, Step 3 using 5-amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide (Example 22, Step 2) (70 mg, 0.23 mmol), 2-(6-bromopyridin-3-yl)propan-2-ol (for preparation, see WO 2004/050024 A2Example 120 Step A) (50 mg, 0.23 mmol), Pd2(dba)3 (21 mg, 0.023 mmol), X-PHOS (55 mg, 0.12 mmol), potassium carbonate (35 mg, 0.25 mmol), and tert-amyl alcohol (1.2 mL) as starting materials. 1H NMR (500 MHz, d6-DMSO): δ 11.19 (s, 1H), 8.67 (d, 1H), 8.40 (s, 1H), 8.08 (dd, 1H), 7.80 (dd, 1H), 7.72 (s, 1H), 7.58 (s, 1H), 7.12 (d, 1H), 6.93 (d, 1H), 5.13 (s, 1H), 3.70 (m, 4H), 3.53 (m, 4H), 1.43 (s, 6H). LRMS (APCI) calc'd for C21H25N6O3S [M+H]+ 441.2, found 441.0.

Sources & evidence

ORD record
ord-d233cfd6874c414f806d01e56eb88c9c
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

Loading…