Hydrochloric Acid → HCID 86281522, compound

HRID 2178492Notes

Reaction equation

HRID 2178492 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([NH2:28])[C:16]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=2)=[CH:17][CH:18]=1.[C:29]1(=[O:39])[C@@H:37]2[C@@H:32]([CH2:33][CH2:34][CH2:35][CH2:36]2)[C:31](=O)[O:30]1.CCN(C(C)C)C(C)C.Cl>C(#N)C>[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]2[N:19]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([Br:27])=[CH:25][CH:26]=3)[C:31]([C@H:32]3[CH2:33][CH2:34][CH2:35][CH2:36][C@H:37]3[C:29]([OH:39])=[O:30])=[N:28][C:15]=2[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 641660Hexahydrophthalic anhydride, cis-HCID 90416080HCID 90416080, compound

Product 1

HCID 86281522HCID 86281522, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 4 mL microwave vial were added 4-(benzo[d]thiazol-2-ylmethoxy)-N1-(4-bromobenzyl)benzene-1,2-diamine hydrochloride (100 mg, 0.21 mmol), cis-hexahydroisobenzofuran-1,3-dione (34 mg, 0.21 mmol), DIPEA (27 mg, 0.21 mmol), and acetonitrile (2 mL). The mixture was irradiated for 1 h at 82° C. in a microwave reactor. The reaction was cooled to RT, HCl (1 mL, 6 N) was added and the reaction was irradiated for 1 h at 82° C. in a microwave reactor. The reaction was cooled to RT and the solid byproducts were removed by filtration and filtrate was purified using reverse phase HPLC to provide the title compound. MS (ESI): mass calcd. for C29H26BrN3O3S, 575.10; m/z found, 576.1 [M+H]+. 1H-NMR (500 MHz, CDCl3) δ 8.03 (d, J=8.0, 1H), 7.89 (d, J=8.0, 1H), 7.56-7.48 (m, 4H), 7.45-7.38 (m, 2H), 7.19-7.16 (m, 1H), 7.16-7.11 (m, 1H), 6.97 (d, J=8.4, 2H), 5.59-5.49 (m, 1H), 5.46 (s, 2H), 3.40-3.24 (m, 1H), 2.93 (d, J=4.5, 1H), 2.39-2.19 (m, 2H), 1.96-1.83 (m, 2H), 1.82-1.69 (m, 1H), 1.65-1.50 (m, 2H), 1.35 (d, J=13.0, 1H).

Workup

  1. customThe mixture was irradiated for 1 h at 82° C. in a microwave reactor
  2. customthe reaction was irradiated for 1 h at 82° C. in a microwave reactor
  3. temperatureThe reaction was cooled to RT
  4. customthe solid byproducts were removed by filtration and filtrate
  5. customwas purified

Sources & evidence

ORD record
ord-a8a6ac2fce5c49c291da47bdbaf52dd0
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

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