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

HRID 2060640Notes

Reaction equation

HRID 2060640 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].Cl[C:23]1[N:28]=[C:27]([CH3:29])[C:26]([C:30]([OH:33])([CH3:32])[CH3:31])=[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:33][C:30]([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][C:27]=1[CH3:29])([CH3:32])[CH3:31]

Participants

7

Reactant 5

HCID 64052-Methyl-2-butanolHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 583352605-Amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamideHCID 583352662-(6-Chloro-2-methylpyridin-3-yl)propan-2-ol

Product 1

HCID 446231755-{[5-(1-Hydroxy-1-methylethyl)-6-methylpyridin-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 1, Step 2 using 5-amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxamide (Example 22, Step 2) (104 mg, 0.34 mmol), 2-(6-chloro-2-methylpyridin-3-yl)propan-2-ol (Example 13, Step 1) (63 mg, 0.34 mmol), Pd2(dba)3 (31 mg, 0.034 mmol), X-PHOS (81 mg, 0.17 mmol), potassium carbonate (47 mg, 0.34 mmol), and tert-amyl alcohol (0.68 mL) as starting materials. 1H NMR (500 MHz, d6-DMSO): δ 11.10 (s, 1H), 8.69 (d, 1H), 8.08 (dd, 1H), 7.72 (d, 1H), 7.68 (s, 1H), 7.56 (s, 1H), 6.93 (d, 1H), 6.92 (d, 1H), 5.01 (s, 1H), 3.70 (m, 4H), 3.53 (m, 4H), 2.74 (s, 3H), 1.49 (s, 6H). LRMS (APCI) calc'd for C22H27N6O3S [M+H]+ 455.2, found 455.1.

Sources & evidence

ORD record
ord-f4d88aadd4b54351948f163e30c4ad9f
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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