Trifluoroacetic acid → HCID 18697923, compound

HRID 2289488Notes

Reaction equation

HRID 2289488 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27]4[CH:28]=[CH:29][C:30]5[N:31]([CH2:40][CH3:41])[C:32]6[C:37]([C:38]=5[CH:39]=4)=[CH:36][CH:35]=[CH:34][CH:33]=6)[N:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:40]([N:31]1[C:30]2[CH:29]=[CH:28][C:27]([NH:26][C:22]3[N:21]=[C:20]([C:17]4[CH:18]=[CH:19][C:14]([N:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)=[N:15][CH:16]=4)[CH:25]=[CH:24][N:23]=3)=[CH:39][C:38]=2[C:37]2[C:32]1=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH3:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18697926HCID 18697926, compound

Product 1

HCID 18697923HCID 18697923, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-(4-tert-butoxycarbonylpiperazin-1-yl)pyrid-5-yl)-N-(9-ethylcarbazol-3-yl)-2-pyrimidineamine (65 mg, 0.12 mmol) in dichloromethane (2 ml) was treated with trifluoroacetic acid (2 ml). After 2h the mixture was evaporated and the residue reconcentrated five times from dichloromethane then three times from diethyl ether. The residue was subjected to column chromatography (silica, 0.88 ammonia solution-methanol-dichloromethane 1:5:94) to afford the title compound (28 mg) as a pale yellow solid m.p. 131-137°. δH (d6DMSO) 1.31 (3H, t, J 7.1 Hz), 2.80 (4H, m), 3.56 (4H, m), 4.42 (2H, q, J 7.1 Hz), 6.93 (1H, d, J 9.1 Hz), 7.17 (1H, m), 7.25 (1H, d, J 5.3 Hz), 7.43 (1H, m), 7.55 (2H, m), 7.76 (1H, dd, J 2.9, 8.8 Hz), 8.03 (1H, d, J 7.4 Hz), 8.27 (1H, dd, J 2.1, 9.1 Hz), 8.41 (1H, d, J 5.3 Hz), 8.57 (1H, d, J 1.8 Hz), 8.95 (1H, d, J 2.1 Hz) and 9.45 (1H, s).

Workup

  1. customAfter 2h the mixture was evaporated

Sources & evidence

ORD record
ord-a2f3aafaf3d64bd1939be556e6186341
Source dataset
uspto-grants-2000_07
Patent number
US06093716

Reaction notes

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