1,2-Dimethoxyethane → HCID 68079206, compound

HRID 1522408Notes

Reaction equation

HRID 1522408 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=2[CH3:26])=[O:17])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:37]2[CH:46]=[CH:45][C:40]3[NH:41][C:42](=[O:44])[NH:43][C:39]=3[CH:38]=2)O1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O>[CH3:13][C:12]([N:8]1[C:6]2[N:7]=[C:2]([C:37]3[CH:46]=[CH:45][C:40]4[NH:41][C:42](=[O:44])[NH:43][C:39]=4[CH:38]=3)[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]3[C:21](=[O:28])[NH:22][C:23]([CH3:27])=[CH:24][C:25]=3[CH3:26])=[O:17])[C:5]=2[C:10]([CH3:11])=[N:9]1)([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 438110655-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-oneHCID 565974276-Chloro-1-(1,1-dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Product 1

HCID 68079206HCID 68079206, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Procedure

The title compound was prepared in the same manner as described in example 74 using 6-chloro-1-(1,1-dimethylethyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.174 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-benzimidazol-2-one (58.9 mg, 0.226 mmol), DME (3 mL), water (1.00 mL), sodium carbonate (0.261 mL, 0.523 mmol) and PdCl2(dppf)-CH2Cl2 adduct (11.38 mg, 0.014 mmol) wherein the reaction time was 40 min. The crude product was purified by column chromatography (eluent: gradient of 0 to 15% (9:1 MeOH/NH4OH)/DCM). The final product was collected as a solid, 24 mg (27%). LCMS E-S (M+H)=500.2 1H NMR (400 MHz, DMSO-d6) δ ppm 1.77 (m, 9 H), 2.12 (s, 3 H), 2.24 (s, 3 H), 2.40 (s, 3 H), 4.38 (d, J=4.55 Hz, 2 H), 5.89 (s, 1 H), 7.06 (d, J=8.08 Hz, 1 H), 7.59 (s, 1 H), 7.72-7.86 (m, 2 H), 8.73 (br. s., 2 H), 10.74-10.92 (m, 1 H), 11.53 (br. s., 1 H).

Workup

  1. customThe crude product was purified by column chromatography (eluent: gradient of 0 to 15% (9:1 MeOH/NH4OH)/DCM)
  2. customThe final product was collected as a solid, 24 mg (27%)

Sources & evidence

ORD record
ord-80ac3dd55a4244f5899813bf5fd36c37
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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