Hydrochloric Acid → 6-((1R,2S)-2-Aminocyclohexylamino)-7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 516002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516002
[Cl:1][C:2]1[C:3]2[CH2:31][NH:30][C:29](=[O:32])[C:4]=2[C:5]([C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15]C(=O)OC(C)(C)C.Cl>CC(O)=O>[NH2:15][C@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]1[NH:8][C:7]1[N:6]=[C:5]([C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)[C:4]2[C:29](=[O:32])[NH:30][CH2:31][C:3]=2[C:2]=1[Cl:1]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86654711tert-Butyl (1S,2R)-2-(7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate

Produkt 1

HCID 532522786-((1R,2S)-2-Aminocyclohexylamino)-7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (1S,2R)-2-(7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (10.00 mg, 0.022 mmol) in HCl (0.5 mL, 16.46 mmol) and HOAc (1 mL) was stirred at RT for 30 min. The reaction mixture was concentrated and the resulting residue was washed with IPE to give the HCl salt of the title compound (5 mg, 63.9%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.48-1.97 (m, 8 H), 3.72-3.78 (m, 1 H), 3.96 (br s, 3 H), 4.35 (d, J=4.88 Hz, 2 H), 4.57 (br s, 1 H), 6.29 (d, J=6.83 Hz, 1 H), 7.93 (br s, 2 H), 8.40-8.45 (m, 1 H), 8.49 (s, 1 H), 8.98 (s, 1 H). [M+H] calc'd for C17H21ClN6O, 361; found, 361.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. washthe resulting residue was washed with IPE

Quellen und Nachweise

ORD-Eintrag
ord-4eb0ae09e6264472af2b0ae561b72448
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108970B2

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