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 711467Notes

Reaction equation

HRID 711467 reaction equation
[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]

Participants

4

Reactant 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

Product 1

HCID 532522786-((1R,2S)-2-Aminocyclohexylamino)-7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneYield 63.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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, 8H), 3.72-3.78 (m, 1H), 3.96 (br s, 3H), 4.35 (d, J=4.88 Hz, 2H), 4.57 (br s, 1H), 6.29 (d, J=6.83 Hz, 1H), 7.93 (br s, 2H), 8.40-8.45 (m, 1H), 8.49 (s, 1H), 8.98 (s, 1H). [M+H] calc'd for C17H21ClN6O, 361. found, 361.

Workup

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

Sources & evidence

ORD record
ord-d07d7749177d4f3cae4cfc8d29b1a708
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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