Hydrochloric Acid → 6-((1R,2S)-2-Aminocyclopentylamino)-4-(3-(methylsulfonyl)phenylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 711484Notes

Reaction equation

HRID 711484 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12]2[C:17]3[C:18](=[O:21])[NH:19][CH2:20][C:16]=3[CH:15]=[C:14]([NH:22][C@@H:23]3[CH2:27][CH2:26][CH2:25][C@@H:24]3[NH:28]C(=O)OC(C)(C)C)[N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].Cl>CC(O)=O>[NH2:28][C@H:24]1[CH2:25][CH2:26][CH2:27][C@H:23]1[NH:22][C:14]1[N:13]=[C:12]([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=2)[C:17]2[C:18](=[O:21])[NH:19][CH2:20][C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86654717tert-Butyl (1S,2R)-2-(4-(3-(methylsulfonyl)phenylamino)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclopentylcarbamate

Product 1

HCID 532524396-((1R,2S)-2-Aminocyclopentylamino)-4-(3-(methylsulfonyl)phenylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneYield 67%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of tert-butyl (1S,2R)-2-(4-(3-(methylsulfonyl)phenylamino)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclopentylcarbamate (16.5 mg, 0.329 mmol) and HCl (1 mL, 32.9 mmol) in HOAc (2 mL) was stirred at RT for 3 h. The mixture was concentrated under reduced pressure and the residue was recrystallized from EtOH-H2O to give the title compound (9.6 mg, 67%). 1H-NMR (DMSO-d6) δ ppm 1.63-1.79 (m, 4H), 20.3-2.06 (m, 1H), 2.19-2.20 (m, 1H), 3.32 (s, 3H), 3.74 (br s, 1H), 4.23-4.28 (m, 2H), 4.45 (br s, 1H), 6.22 (s, 1H), 7.34-7.35 (m, 1H), 7.51-7.58 (m, 3H), 7.73 (br s, 3H), 8.13 (s, 1H), 8.82 (s, 1H), 9.26 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was recrystallized from EtOH-H2O

Sources & evidence

ORD record
ord-0a03552f6f374bb2acec859770918342
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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