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

HRID 857754Notes

Reaction equation

HRID 857754 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH2:8][NH2:9])[CH:5]=[N:4][N:3]=[N:2]1.C([N:21]1[CH2:28][CH2:27][CH2:26][C@H:22]1[C:23]([OH:25])=[O:24])(OC(C)(C)C)=O.C(Cl)C[Cl:31]>>[Cl:31][C:11]1[CH:12]=[CH:13][C:6]([N:1]2[CH:5]=[N:4][N:3]=[N:2]2)=[C:7]([CH:10]=1)[CH2:8][NH:9][C:23](=[O:24])[C@@H:22]1[CH2:26][CH2:27][CH2:28][NH:21]1.[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH2:8][NH:9][C:23](=[O:25])[C@@H:22]2[CH2:26][CH2:27][CH2:28][NH:21]2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 11159614HCID 11159614, compound

Product 2

HCID 69655818N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamideHCID 69656336HCID 69656336, compound

Procedure

The title compound was prepared essentially according to the EDC coupling procedure described in Example 26 using 1-[2-(1H-tetraazol-1-yl)phenyl]methanamine (Example 1, 55 mg, 0.31 mmol) and Boc-L-proline (67 mg, 0.31 mmol) followed by purification of the intermediate (silica gel chromatography, 50%–70% EtOAc/hexanes) and deprotection using 4.0 M HCl in dioxane. The hydrochloride salt of the title compound was isolated as a colorless gum: LCMS (M+H): 273.1. 1H NMR (CD3OD, 400 MHz): δ 9.58 (s, 1 H), 7.66–7.65 (m, 2 H), 7.59–7.55 (m, 1 H), 7.51–7.49 (m, 1 H), 4.39–4.26 (m, 2 H), 4.16 (m, 1 H), 3.31–3.28 (m, 2 H), 2.36–2.33 (m, 1 H), 1.98–1.87 (m, 3 H).

Workup

  1. customThe title compound was prepared essentially
  2. customfollowed by purification of the intermediate (silica gel chromatography, 50%–70% EtOAc/hexanes) and deprotection

Sources & evidence

ORD record
ord-f54668f42a194d2f80da6f6265695de8
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

Loading…