2-Methyl-2-butanol → Ethyl 5-{[6-(2-hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

HRID 2060633Notes

Reaction equation

HRID 2060633 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]([O:21][CH2:22][CH3:23])=[O:20].Br[C:25]1[N:30]=[C:29]([CH:31]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH2:32][OH:33])[CH:28]=[CH:27][CH:26]=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][CH2:32][CH:31]([C:29]1[N:30]=[C:25]([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]([O:21][CH2:22][CH3:23])=[O:20])[CH:26]=[CH:27][CH:28]=1)[N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

7

Reactant 5

HCID 64052-Methyl-2-butanolHCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58335250Ethyl 5-amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylateHCID 583352752-(6-Bromopyridin-2-yl)-2-morpholin-4-ylethanol

Product 1

HCID 67305910Ethyl 5-{[6-(2-hydroxy-1-morpholin-4-ylethyl)pyridin-2-yl]amino}-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

The title compound was prepared as described in Example 3, Step 1 using ethyl 5-amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate (114 mg, 0.34 mmol), 2-(6-bromopyridin-2-yl)-2-morpholin-4-ylethanol (Example 3, Step 1) (98 mg, 0.34 mmol), Pd2(dba)3 (9.4 mg, 10.2 μmol), X-PHOS (24.4 mg, 0.051 mmol), potassium carbonate (51.8 mg, 0.38 mmol), and tert-amyl alcohol (1.7 ml) as starting materials. LRMS (APCI) calc'd for (C26H33N6O5S) [M+H]+, 541.2; found 541.1.

Sources & evidence

ORD record
ord-3f3839104f9c4210a8c392401c5fb439
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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