Hydrochloric Acid → Hydrochloric Acid

HRID 470185Notes

Reaction equation

HRID 470185 reaction equation
[F:1][C:2]1[C:3]2[N:11]([C@H:12]3[C@H:19]4[C@H:15]([O:16]C(C)(C)[O:18]4)[CH2:14][CH:13]3[F:22])[CH:10]=[N:9][C:4]=2[C:5]([NH2:8])=[N:6][CH:7]=1.[ClH:23]>CO>[NH2:8][C:5]1[C:4]2[N:9]=[CH:10][N:11]([C@@H:12]3[CH:13]([F:22])[CH2:14][C@@H:15]([OH:16])[C@H:19]3[OH:18])[C:3]=2[C:2]([F:1])=[CH:7][N:6]=1.[ClH:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 583293087-fluoro-1-((3aS,4S,6aR)-5-fluoro-2,2-dimethyltetrahydro-3aH-cyclopenta [d][1,3]dioxol-4-yl)-1H-imidazo [4,5-c]pyridin-4-amine

Product 2

HCID 313Hydrochloric AcidHCID 45111033(1R,2S,3S)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)-4-fluorocyclopentane-1,2-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-fluoro-1-((3aS,4S,6aR)-5-fluoro-2,2-dimethyltetrahydro-3aH-cyclopenta [d][1,3]dioxol-4-yl)-1H-imidazo[4,5-c]pyridin-4-amine (5-12) (30 mg, 0.1 mmol, 1 equiv) was dissolved in MeOH (1 mL) and concentrated HCl (200 uL) was added. After disappearance of the starting material, the mixture was concentrated to afford (1R,2S,3S)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)-4-fluorocyclopentane-1,2-diol (5-13) as a white solid of the bis-HCl salt. 1H NMR (500 MHz, CD3OD): δ 8.59 (s, 1H); 7.82 (d, J=5.0 Hz, 1H); 5.31-5.38 (m, 1 H); 5.28 (d, J=8.5 Hz, 1H); 4.35 (m, 1H); 4.19 (t, J=5.0 Hz, 1H); 2.63 (m, 1H); 2.05 (dd, J=27.5, 16.5 Hz, 1H). LRMS m/z (M+H) 270.9 found, 271.1 required.

Workup

  1. concentrationAfter disappearance of the starting material, the mixture was concentrated

Sources & evidence

ORD record
ord-5cd235551b5d4fdeba7e0dccffa7730b
Source dataset
uspto-grants-2014_01
Patent number
US08629275B2

Reaction notes

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