Hydrochloric Acid → Hydrochloric Acid

HRID 470167Notes

Reaction equation

HRID 470167 reaction equation
[ClH:1].CC1(C)[O:7][C@@H:6]2[CH2:8][CH2:9][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[CH2:9][CH2:8][C@@H:6]([OH:7])[C@H:5]3[OH:4])[C:19]=2[C:18]([F:20])=[CH:17][N:16]=1.[ClH:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 672306201-[(3aS,4R,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-7-fluoro-1H-imidazo[4,5-c]pyridin-4-amine

Product 2

HCID 313Hydrochloric AcidHCID 46174640(1R,2S,3R)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Concentrated HCl (5 mL) was added to 1-((3aS,4R,6aR)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-7-fluoro-1H-imidazo[4,5-c]pyridin-4-amine (1-7) (2.3 g, 7.9 mmol, 1 equiv) in methanol (60 mL). After disappearance of the starting material as monitored by LC-MS analysis, the mixture was concentrated to afford (1R,2S,3R)-3-(4-amino-7-fluoro-1H-imidazo[4,5-c]pyridin-1-yl)cyclopentane-1,2-diol (1-9) as a tan solid of the bis-HCl salt. 1H NMR (1-9) (500 MHz, DMSO): δ 8.76 (s, 1H); 8.55 (s, 2H); 8.03 (d, J=5.5 Hz, 1H); 4.88 (q, J=9.3 Hz, 1H); 4.19 (dd, J=9.4, 4.0 Hz, 1H); 4.00 (t, J=4.5 Hz, 1H); 2.41-2.31 (m, 1H); 2.15-2.06 (m, 1H); 1.92-1.83 (m, 1H); 1.66 (ddd, J=14.0, 9.7, 4.9 Hz, 1H). HRMS m/z (M+H) 253.1093 found, 253.1095 required. 1H NMR (1-10) (500 MHz, DMSO): δ 8.95 (s, 1H); 8.14 (s, 2H); 8.06 (d, J=4.5 Hz, 1H); 4.96 (q, J=8.4 Hz, 1H); 4.10 (dd, J=8.7, 4.8 Hz, 1H); 4.02 (d, J=4.4 Hz, 1H); 2.38-2.29 (m, 1H); 2.20-2.11 (m, 2H); 1.72-1.65 (m, 1H). HRMS m/z (M+H) 253.1095 found, 253.1095 required.

Workup

  1. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-c022bcdea6d449e2ad91e999742be5c5
Source dataset
uspto-grants-2014_01
Patent number
US08629275B2

Reaction notes

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