Diisopropylethylamine → HCID 86727254, compound

HRID 2173057Notes

Reaction equation

HRID 2173057 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:18])[N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10][C:6]=2[C:5]([F:19])=[C:4](Cl)[N:3]=1.[NH2:21][C@@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C@@H:23]1[NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].[CH3:36]CN(C(C)C)C(C)C>CC(O)C.CS(C)=O>[C:31]([O:30][C:29]([NH:28][C@H:23]1[CH2:24][CH2:25][CH2:26][CH2:27][C@H:22]1[NH:21][C:4]1[N:3]=[C:2]([Cl:1])[C:7]2[C:8](=[O:18])[N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:10]([CH3:36])[C:6]=2[C:5]=1[F:19])=[O:35])([CH3:32])([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514389(1S,2R)-Cyclohexane-1,2-diamine, N1-BOC protectedHCID 86654739tert-Butyl 4,6-dichloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate

Product 1

HCID 86727254HCID 86727254, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3776IsopropanolSolvent

Procedure

To a flask containing a mixture of tert-butyl 4,6-dichloro-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (1 g, 2.98 mmol) in 2-propanol (7 mL) was added tert-butyl ((1S,2R)-2-aminocyclohexyl)carbamate (767 mg, 3.58 mmol) dissolved in DMSO (1.2 mL) followed by DIPEA (0.677 mL, 3.88 mmol). The flask was equipped with a condenser and nitrogen blanket and was lowered into a 90° C. oil bath, where the reaction mixture was allowed to stir for 16 h. The mixture was subsequently purified via preparative HPLC to give the title compound as a white solid (490 mg, 32%). [M+H] calc'd for C19H26ClFN4O3, 413. found, 413.

Workup

  1. additionTo a flask containing
  2. customThe flask was equipped with a condenser
  3. customwas lowered into a 90° C.
  4. customThe mixture was subsequently purified via preparative HPLC

Sources & evidence

ORD record
ord-52ecbf41c87c4572a1d253b88f4d38df
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

Loading…