Hydrochloric Acid → Hydrochloric Acid

HRID 470170Notes

Reaction equation

HRID 470170 reaction equation
[ClH:1].CC1(C)[O:7][C@@H:6]2[CH:8]=[CH:9][C@@H:10]([N:11]3[C:19]4[C:18]([F:20])=[CH:17][N:16]=[C:15]([NH2:21])[C:14]=4[N:13]=[CH:12]3)[C@@H:5]2[O:4]1>CO>[NH2:21][C:15]1[C:14]2[N:13]=[CH:12][N:11]([C@H:10]3[C@H:5]([OH:4])[C@H:6]([OH:7])[CH:8]=[CH:9]3)[C:19]=2[C:18]([F:20])=[CH:17][N:16]=1.[ClH:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 672351381-[(3aS,4R,6aR)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-7-fluoro-1H-imidazo[4,5-c]pyridin-4-amine

Product 2

HCID 313Hydrochloric AcidHCID 45111036(1S,2R,5R)-5-(4-amino-7-fluoroimidazo[4,5-c]pyridin-1-yl)cyclopent-3-ene-1,2-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated HCl (3 mL) was added to 1-[(3aS,4R,6aR)-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-7-fluoro-1H-imidazo[4,5-c]pyridin-4-amine (2-3) (158 mg, 0.54 mmol, 1 equiv) in methanol (10 mL). After disappearance of the starting material, as monitored by LC-MS analysis, the mixture was concentrated to afford (1S,2R,5R)-5-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopent-3-ene-1,2-dial (2-5) as a yellow solid of the bis-HCl salt. 1H NMR (2-5) (500 MHz, DMSO): δ 8.57 (s, 2H); 8.52 (s, 1H); 8.03 (d, J=5.3 Hz, 1H); 6.23 (d, J=5.9 Hz, 1H); 6.09 (d, J=6.2 Hz, 1H); 5.53 (d, J=5.5 Hz, 1H); 4.51 (s, 1H); 4.13 (t, J=5.7 Hz, 1H). HRMS m/z (M+H) 251.0939 found, 251.0939 required. 1H NMR (2-6) (500 MHz, DMSO): δ 8.53 (s, 1H); 8.24 (s, 2H); 8.08 (d, J=4.5 Hz, 1H); 6.32 (d, J=5.9 Hz, 1H); 6.21 (d, J=6.2 Hz, 1H); 5.71 (s, 1H); 4.54 (d, J=5.7 Hz, 1H); 4.08 (m, 1H). HRMS m/z (M+H) 251.0938 found, 251.0939 required.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-de0f5d00bdcd4e569b819d59a9f45a50
Source dataset
uspto-grants-2014_01
Patent number
US08629275B2

Reaction notes

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