Diisopropylethylamine → HCID 178481287, compound

HRID 707362Notes

Reaction equation

HRID 707362 reaction equation
C(OC(=O)N[C@H]1C[C@H:10]([NH:12][C:13]2S[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)C1)(C)(C)C.Cl.[NH2:24][C@H:25]1[CH2:28][C@H:27]([N:29]2[C:33]3=[N:34][CH:35]=[CH:36][CH:37]=[C:32]3[N:31]([CH3:38])[C:30]2=[O:39])[CH2:26]1.ClC1N(C)C2C=CC=CC=2N=1.C(N(C(C)C)CC)(C)C>CN(C)C1C=CN=CC=1.CS(C)=O>[CH3:38][N:31]1[C:32]2[C:33](=[N:34][CH:35]=[CH:36][CH:37]=2)[N:29]([C@H:27]2[CH2:28][C@H:25]([NH:24][C:13]3[N:12]([CH3:10])[C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)[CH2:26]2)[C:30]1=[O:39]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6630802-chloro-1-methyl-1H-1,3-benzodiazoleHCID 178454113HCID 178454113, compoundHCID 178478929HCID 178478929, compound

Product 1

HCID 178481287HCID 178481287, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was synthesized following the procedure described for INTERMEDIATE 10, using 3-(trans-3-aminocyclobutyl)-1-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one hydrochloride (0.147 g, 0.577 mmol), 2-chloro-1-methyl-1 h-benzoimidazole (0.096 g, 0.577 mmol), diisopropylethylamine (1 ml, 5.75 mmol) and 4-dimethylaminopyridine (7.05 mg, 0.058 mmol) in DMSO (0.5 mL) and purified by ISCO on silica gel column using 0-80% EtOAc/hexanes to afford 1-methyl-3-(trans-3-((1-methyl-1H-benzo[d]imidazol-2-yl)amino)cyclobutyl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.103 g, 0.296 mmol, 51.2% yield). m/z: 366.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ: ppm 8.04 (dd, J=5.28, 1.17 Hz, 1 H), 7.50 (dd, J=7.82, 1.17 Hz, 1 H), 7.19-7.24 (m, 1 H), 7.13-7.18 (m, 1 H), 7.10 (dd, J=7.73, 5.18 Hz, 1 H), 7.02 (d, J=6.46 Hz, 1 H), 6.88-6.98 (m, 2 H), 5.32 (t, J=8.41 Hz, 1 H), 4.51-4.69 (m, 1 H), 3.56 (s, 3 H), 3.26-3.40 (m, 5 H), 2.41-2.57 (m, 2 H).

Workup

  1. customThe title compound was synthesized
  2. custompurified by ISCO on silica gel column

Sources & evidence

ORD record
ord-89582d7246cf439eb9aa62e3975bebae
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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