2-Methyl-2-butanol → 2-[4-(1-Hydroxy-1-methylethyl)phenyl]-5-[(6-methyl-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-2-yl)amino]-1,3-thiazole-4-carboxamide

HRID 2060614Notes

Reaction equation

HRID 2060614 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].Cl[C:21]1[N:26]=[C:25]2[CH2:27][N:28]([CH3:31])[C:29](=[O:30])[C:24]2=[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[N:26]=[C:25]4[CH2:27][N:28]([CH3:31])[C:29](=[O:30])[C:24]4=[CH:23][CH:22]=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 582166242-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-oneHCID 583352645-Amino-2-[4-(1-hydroxy-1-methylethyl)phenyl]-1,3-thiazole-4-carboxamide

Product 1

HCID 446230412-[4-(1-Hydroxy-1-methylethyl)phenyl]-5-[(6-methyl-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]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 8, Step 6 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-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one (123 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 (600 MHz, d6-DMSO) δ 11.63 (s, 1H), 7.87 (m, 3H), 7.82 (s, 1H), 7.71 (s, 1H), 7.55 (d, 2H), 7.22 (d, 1H), 5.10 (s, 1H), 4.50 (s, 2H), 3.04 (s, 3H), 1.42 (s, 6H). LRMS (APCI) calc'd for C21H22N5O3S [M+H]+ 424.1, found 424.0.

Sources & evidence

ORD record
ord-6d28d334eb3642f7afb9712f5a32c93e
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

Loading…