Hydrochloric Acid → N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

HRID 857780Notes

Reaction equation

HRID 857780 reaction equation
C(OC([N:8]1[CH2:31][CH2:30][CH2:29][C@H:9]1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:15]=1[N:24]1[CH:28]=[N:27][N:26]=[N:25]1)=[O:11])=O)(C)(C)C.[ClH:32]>CCOC(C)=O>[Cl:32][C:18]1[CH:17]=[CH:16][C:15]([N:24]2[CH:28]=[N:27][N:26]=[N:25]2)=[C:14]([CH:19]=1)[CH2:13][NH:12][C:10](=[O:11])[C@@H:9]1[CH2:29][CH2:30][CH2:31][NH:8]1.[N:24]1([C:15]2[CH:16]=[CH:17][C:18]([C:20]([F:23])([F:21])[F:22])=[CH:19][C:14]=2[CH2:13][NH:12][C:10](=[O:11])[C@@H:9]2[CH2:29][CH2:30][CH2:31][NH:8]2)[CH:28]=[N:27][N:26]=[N:25]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69655919HCID 69655919, compound

Product 2

HCID 69655818N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamideHCID 69655977HCID 69655977, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred, cold (0° C.) solution of 1-(tert-butoxycarbonyl)-N-[2-(1H-tetraazol-1-yl)-5-(trifluoromethyl)benzyl]-L-prolinamide (92 mg, 0.209 mmol) in EtOAc (1 mL) was added a freshly-prepared, saturated solution of HCl in EtOAc (6 mL). The mixture was stirred at room temperature for 2 h. The solvent was removed in vacuo and the residue azeotroped with diethyl ether to afford the hydrochloride salt of the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 9.66 (s, 1H), 8.83 (s, 1H), 7.98 (s, 1H), 7.91 (d, J=8.0 Hz, 1H), 7.77 (d, J=8.0 Hz, 1 H), 4.66–4.40 (m, 2H), 4.20 (apparent t, J=8.0 Hz, 1H), 3.40–3.35 (m, 2H), 2.41–2.33 (m, 1H), 2.06–1.88 (m, 3H). LCMS (M+H): 341.1.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with diethyl ether

Sources & evidence

ORD record
ord-29e22fa9ce5f47ffaba85c6de2752247
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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