Diisopropylethylamine → HCID 178481625, compound

HRID 707361Notes

Reaction equation

HRID 707361 reaction equation
C(OC(=O)N[C@H]1C[C@H](NC2SC3C=CC=CC=3N=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.Cl[C:41]1[S:42][C:43]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][C:44]=2[N:45]=1.C(N(C(C)C)CC)(C)C>CN(C)C1C=CN=CC=1.CS(C)=O>[F:50][C:47]1[CH:48]=[CH:49][C:43]2[S:42][C:41]([NH:24][C@H:25]3[CH2:28][C@H:27]([N:29]4[C:33]5=[N:34][CH:35]=[CH:36][CH:37]=[C:32]5[N:31]([CH3:38])[C:30]4=[O:39])[CH2:26]3)=[N:45][C:44]=2[CH:46]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 112408962-Chloro-5-fluoro-1,3-benzothiazoleHCID 178454113HCID 178454113, compoundHCID 178478929HCID 178478929, compound

Product 1

HCID 178481625HCID 178481625, compoundYield 14.07%

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-5-fluorobenzo[d]thiazole (0.108 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 3-(trans-3-((5-fluorobenzo[d]thiazol-2-yl)amino)cyclobutyl)-1-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.030 g, 0.081 mmol, 14.07% yield). m/z: 370.1 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ: ppm 8.07 (d, J=4.89 Hz, 1 H), 7.43-7.60 (m, 1 H), 7.23-7.34 (m, 1 H), 7.17 (d, J=7.43 Hz, 1 H), 6.98-7.10 (m, 1 H), 6.84 (t, J=8.71 Hz, 1 H), 6.18 (br. s., 1 H), 5.40 (quin, J=8.36 Hz, 1 H), 4.62 (br. s., 1 H), 3.50-3.67 (m, 2 H), 3.43 (s, 3 H), 2.55 (t, J=10.07 Hz, 2 H).

Workup

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

Sources & evidence

ORD record
ord-0bc81dda80a3464996b20cf479e34f76
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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