Trifluoroacetic acid → HCID 68830743, compound

HRID 1271447Notes

Reaction equation

HRID 1271447 reaction equation
C([NH:8][C@H:9]1[CH2:13][CH2:12][C@@H:11]([CH2:14][N:15]2[CH:23]=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[CH:21]3)=[N:16]2)[CH2:10]1)(OC(C)(C)C)=O.[C:24]([OH:30])([C:26]([F:29])([F:28])[F:27])=[O:25]>ClCCl>[F:27][C:26]([F:29])([F:28])[C:24]([OH:30])=[O:25].[N:16]1[N:15]([CH2:14][C@@H:11]2[CH2:12][CH2:13][C@H:9]([NH2:8])[CH2:10]2)[CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][CH:20]=[CH:21]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 18453484HCID 18453484, compound

Product 1

HCID 68830743HCID 68830743, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deprotection of N1-BOC-(1S,3R)-3-(2H-indazol-2-ylmethyl)cyclopentan-1-amine (400 mg, 1.27 mmol), the more polar isomer from Step 1, Example 67, using TFA (3 ml) in dry dichloromethane (3 ml) as described in Example 1, Step 2 gave 273 mg of the amine as its TFA salt, which was used as such for the coupling reaction. Step 2: Coupling reaction of Step 1 intermediate (273 mg, 1.27 mmol) with Intermediate 17 (109 mg, 0.63 mmol) in the presence of potassium carbonate (175 mg, 1.27 mmol) and NaI (95 mg, 0.63 mmol) in THF (30 ml) as described in Example 1, Step 3 gave 90 mg of the product as a yellow semisolid; IR (neat) 3317, 3117, 3058, 2943, 2872, 2239, 1660, 1514, 1412, 1306, 1262, 1191, 1157, 1139, 1042, 1009 cm−1; 1H NMR (CDCl3, 300 MHz) δ 1.14–1.29 (m, 2H), 1.53–1.62 (m, 2H), 1.74–1.90 (m, 3H), 1.95–2.32 (m, 5H), 2.67–2.73 (m, 1H), 3.12–3.17 (m, 1H), 3.35 (s, 2H), 3.37–3.59 (m, 2H), 4.38–4.41 (m, 2H), 4.74 (m, 1H), 7.04–7.09 (m, 1H), 7.26–7.30 (m, 1H), 7.64–7.71 (m, 2H), 7.92 (s, 1H).

Sources & evidence

ORD record
ord-081a06f4b14b4ffabbd72b9bee53435c
Source dataset
uspto-grants-2007_04
Patent number
US07205323B2

Reaction notes

Loading…