Trifluoroacetic acid → HCID 68834206, compound

HRID 1271445Notes

Reaction equation

HRID 1271445 reaction equation
C([NH:8][C@H:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][N:15]2[N:19]=[CH:18][CH:17]=[N:16]2)[CH2:10]1)(OC(C)(C)C)=O.[C:20]([OH:26])([C:22]([F:25])([F:24])[F:23])=[O:21]>ClCCl>[F:23][C:22]([F:25])([F:24])[C:20]([OH:26])=[O:21].[N:16]1[N:15]([CH2:14][C@@H:11]2[CH2:12][CH2:13][C@H:9]([NH2:8])[CH2:10]2)[N:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 18453482HCID 18453482, compound

Product 1

HCID 68834206HCID 68834206, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deprotection of N1-BOC-(1S,3R)-3-(2H-1,2,3-triazol-2-ylmethyl)cyclopentan-1-amine (500 mg, 1.87 mmol) using TFA (3 ml) in dry dichloromethane (3 ml) as described in Example 1, Step 2 gave 528 mg of the amine as its TFA salt, which was used as such for the coupling reaction. Step 3: Coupling reaction of Step 2 intermediate (528 mg, 1.87 mmol) with Intermediate 17 (162 mg, 0.94 mmol) in the presence of potassium carbonate (780 g, 5.63 mmol) and NaI (141 mg, 0.94 mmol) in THF (30 ml) as described in Example 1, Step 3 gave 90 mg of the product as a white solid; IR (KBr) 3437, 2955, 2236, 1656, 1420 cm−1; 1H NMR (CDCl3, 300 MHz) δ 1.16–1.25 (m, 1H), 1.46–1.62 (m, 2H), 1.70–1.87 (m, 3H), 1.95–2.34 (m, 5H), 2.54–2.65 (m, 1H), 3.09–3.18 (m, 1H), 3.36–3.62 (m, 4H), 4.43 (d, J=7.2 Hz, 2H), 4.76–4.78 (m, 1H), 7.58 (s, 2H).

Sources & evidence

ORD record
ord-7ba6d80ac0944544b643d8f69ead91fb
Source dataset
uspto-grants-2007_04
Patent number
US07205323B2

Reaction notes

Loading…