Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → HCID 68555585, compound

HRID 1868104Notes

Reaction equation

[CH:1]([CH:4]1[CH2:8][CH2:7][C:6]([CH3:12])([C:9]([OH:11])=O)[CH2:5]1)([CH3:3])[CH3:2].[F:13][C:14]([F:28])([F:27])[C:15]1[C:16]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[N:17][CH:18]=[CH:19][CH:20]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[CH:1]([CH:4]1[CH2:8][CH2:7][C:6]([C:9]([N:24]2[CH2:25][CH2:26][N:21]([C:16]3[C:15]([C:14]([F:28])([F:13])[F:27])=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:22][CH2:23]2)=[O:11])([CH3:12])[CH2:5]1)([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of 3-isopropyl-1-methylcyclopentanecarboxylic acid (89 mg, 0.52 mmol) and 1-(3-(trifluoromethyl)pyridin-2-yl)piperazine (242 mg, 1.04 mmol) in N,N-dimethylformamide (1 mL) was added benzotriazole-1 yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (700 mg, 1.56 mmol). The reaction was heated in a microwave at 150° C. for 5 minutes. The reaction mixture was purified with HPLC to yield 1-[(3-isopropyl-1-methylcyclopentyl)carbonyl]-4-[3-(trifluoromethyl)pyridin-2-yl]piperazine in 42% yield (83.3 mg) as off-white solid.

Workup

customThe reaction mixture was purified with HPLC

Sources & evidence

ORD record: ord-c25b1131c89143f8800fa08e6e60b4c9
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632838B2

Reaction notes

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