Sodium Iodide → HCID 68836076, compound

HRID 1271449Notes

Reaction equation

HRID 1271449 reaction equation
[N:1]1[N:2]([CH2:10][C@H:11]2[CH2:15][CH2:14][C@@H:13]([NH2:16])[CH2:12]2)[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[C:17]([OH:23])([C:19]([F:22])([F:21])[F:20])=[O:18].C(=O)([O-])[O-].[K+].[K+].[Na+].[I-]>C1COCC1>[F:20][C:19]([F:22])([F:21])[C:17]([OH:23])=[O:18].[N:1]1[N:2]([CH2:10][C@H:11]2[CH2:15][CH2:14][C@@H:13]([NH2:16])[CH2:12]2)[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 68836077HCID 68836077, compound

Product 1

HCID 68836076HCID 68836076, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Deprotection of N1-BOC-[(3S,1R)-3-(2H-benzo[d][1,2,3]triazol-2-ylmethyl)cyclopentylamine (420 mg, 1.33 mmol), the more polar isomer obtained from Example 70, Step 1 using TFA (2 ml) in dry dichloromethane (2 ml) as described in Example 1, Step 2 gave 438 mg (100%) of the amine as its TFA salt, which was used as such for the next step. Step 2: Coupling reaction of Step 1 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 (neat) 3325, 2951, 2241, 1662, 1414, 1216, 1033 cm−1; 1H NMR (CDCl3, 300 MHz) δ 1.22–1.33 (m, 1H), 1.54–2.33 (m, 10H), 2.72–2.83 (m, 1H), 3.12–3.21 (m, 1H), 3.31–3.68 (m, 4H), 4.73 (d, J=7.5 Hz, 2H), 4.76 (d, J=4.5 Hz, 1H), 7.35–7.40 (m, 2H), 7.83–7.88 (m, 2H).

Sources & evidence

ORD record
ord-cd8be01c9a6e439cbb4837eb79d263d1
Source dataset
uspto-grants-2007_04
Patent number
US07205323B2

Reaction notes

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