Trifluoroacetic acid → HCID 57563133, compound

HRID 1726202Notes

Reaction equation

HRID 1726202 reaction equation
C([O:5][C:6](=[O:46])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]#[N:45])[CH:39]=2)[CH:16]2[CH2:21][CH2:20][N:19]([CH:22]([CH3:36])[CH2:23][CH2:24][NH:25][C:26](=[O:35])[C:27]3[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=3[CH3:34])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)(C)(C)C.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:44]([C:40]1[CH:39]=[C:38]([CH:43]=[CH:42][CH:41]=1)[CH2:37][N:15]([CH:16]1[CH2:21][CH2:20][N:19]([CH:22]([CH3:36])[CH2:23][CH2:24][NH:25][C:26](=[O:35])[C:27]2[C:28]([CH3:34])=[CH:29][CH:30]=[CH:31][C:32]=2[CH3:33])[CH2:18][CH2:17]1)[C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:46])=[O:5])=[CH:10][CH:11]=1)#[N:45]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57563141HCID 57563141, compound

Product 1

HCID 57563133HCID 57563133, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of COMPOUND 143 in CH2Cl2 (2 mL) was added anisole (0.1 mL, 0.92 mmol) followed by TFA (2 mL) and the solution was stirred at room temperature for 90 minutes to afford COMPOUND 149 as a white solid (200 mg, 52%) after a basic work-up and purification. 1H NMR (CD3OD) δ 1.29 (d, 3H, J=6.3 Hz), 1.76-1.89 (m, 5H), 2.07-2.28 (m, 1H), 2.28 (s, 6H), 2.86-3.03 (m, 2H), 3.19-3.27 (m, 3H), 3.37-3.51 (m, 2H), 3.67-3.75 (m, 1H), 4.19 (s, 2H), 4.24 (s, 2H), 6.76 (s, 4H), 7.02 (d, 2H, J=7.5 Hz), 7.11-7.16 (m, 1H), 7.36-7.41 (m, 1H), 7.48-7.55 (m, 3H). 13C NMR (CD3OD) δ 12.82, 18.45, 27.43, 31.16, 36.74, 46.73, 49.61, 50.48, 56.06, 59.61, 67.86, 112.19, 115.51, 118.98, 119.18, 127.52, 128.96, 129.51, 130.55, 130.77, 132.17, 134.23, 137.73, 142.53, 142.92, 152.96, 172.43, 176.24. ES-MS m/z 569 (M+H). Anal. Calcd. for C34H40N4O4.0.6CH2Cl2: C, 67.06; H, 6.70; N, 9.04. Found. C, 66.95; H, 6.64; N, 8.91.

Sources & evidence

ORD record
ord-2fbd94dc3e5145dabeec51819ee75ead
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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