Trifluoroacetic acid → HCID 18453453, compound

HRID 1271448Notes

Reaction equation

HRID 1271448 reaction equation
[N:1]1([CH2:10][C@H:11]2[CH2:15][CH2:14][C@@H:13]([NH2:16])[CH2:12]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][NH:2]1.[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18]>ClCCl>[F:20][C:19]([F:22])([F:21])[C:17]([OH:23])=[O:18].[N:1]1([CH2:10][C@H:11]2[CH2:15][CH2:14][C@@H:13]([NH2:16])[CH2:12]2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][NH:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 18453454HCID 18453454, compound

Product 1

HCID 18453453HCID 18453453, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deprotection of N1-BOC-[(3S,1R)-3-(2H-benzo[d][1,2,3]triazol-1-ylmethyl)cyclopentylamine (420 mg, 1.33 mmol), the less polar isomer from Step 1 using TFA (2 ml) in dry dichloromethane (2 ml) as described in Example 1, Step 2 gave 438 mg of the amine as its TFA salt, which was used as such for the next step. Step 3: Coupling reaction of Step 2 intermediate (438 mg, 1.33 mmol) with Intermediate 17 (160 mg, 0.93 mmol) in the presence of potassium carbonate (735 mg, 5.32 mmol) and NaI (140 mg, 0.93 mmol) in THF (30 ml) as described in Example 1, Step 3 gave 100 mg of the product as a white solid; IR (KBr) 3317, 2928, 2239, 1659, 1416, 1266 cm−1; 1H NMR (CDCl3, 300 MHz) δ 1.23–1.33 (m, 1H), 1.57–1.66 (m, 2H), 1.70–2.03 (m, 5H), 2.14–2.31 (m, 3H), 2.63–2.74 (m, 1H), 3.16–3.19 (m, 1H), 3.30–3.67 (m, 2H), 3.36 (d, J=6.6 Hz, 2H), 4.56–4.77 (m, 3H), 7.26–7.39 (m, 1H), 7.45–7.56 (m, 2H), 8.06 (d, J=8.1 Hz, 1H).

Sources & evidence

ORD record
ord-e7f3666771eb475fad321abecce86a2d
Source dataset
uspto-grants-2007_04
Patent number
US07205323B2

Reaction notes

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