2-Chlorobenzothiazole → HCID 178429377, compound

HRID 707363Notes

Reaction equation

HRID 707363 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[CH:15][C:10]=3[C:9]([CH3:17])([CH3:16])[C:8]2=[O:18])[CH2:4]1.Cl[C:20]1[S:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.O>[S:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[NH:2][C@H:3]1[CH2:6][C@H:5]([N:7]2[C:11]3[N:12]=[CH:13][N:14]=[CH:15][C:10]=3[C:9]([CH3:16])([CH3:17])[C:8]2=[O:18])[CH2:4]1

Participants

6

Reactant 3

HCID 119872-ChlorobenzothiazoleHCID 81531DiisopropylethylamineHCID 178429370HCID 178429370, compound

Product 1

HCID 178429377HCID 178429377, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 7-(trans-3-aminocyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one hydrochloride, INTERMEDIATE 62, (0.100 g, 0.372 mmol), 2-chlorobenzothiazole (0.095 mL, 0.558 mmol), and N,N-diisopropylethylamine (0.194 mL, 1.116 mmol) in DMSO (0.4 mL) was stirred at 120° C. for 4 h. The reaction was allowed to cool to room temperature, diluted with water and extracted with EtOAc. EtOAc was concentrated and residue purified with ISCO using silica gel column eluting with 0-60% EtOAc/hexane to give the title compound 7-(trans-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)-5,5-dimethyl-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one (0.082 g, 0.224 mmol, 60.3% yield) as brown solid. m/z: 366.0 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.84 (s, 1 H), 8.33 (s, 1 H), 7.60 (dd, J=13.11, 7.82 Hz, 2 H), 7.23-7.39 (m, 1 H), 6.99-7.18 (m, 1 H), 6.26 (br. s., 1 H), 5.15-5.40 (m, 1 H), 4.53-4.70 (m, 1 H), 3.33-3.55 (m, 2 H), 2.41-2.58 (m, 2 H), 1.36-1.55 (m, 6 H).

Workup

  1. extractionextracted with EtOAc
  2. concentrationEtOAc was concentrated
  3. customresidue purified with ISCO
  4. washeluting with 0-60% EtOAc/hexane

Sources & evidence

ORD record
ord-29496e0a39e042198242581a1205d9ed
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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