Trifluoroacetic acid → HCID 49785919, compound

HRID 1812334Notes

Reaction equation

COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:32]([N:37]4[CH2:42][CH2:41][N:40](C(OC(C)(C)C)=O)[CH2:39][CH2:38]4)[C:33]([F:36])([F:35])[F:34])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=3)[N:10]=2)=CC=1.FC(F)(F)C(O)=O.F[C:69](F)(F)[S:70](O)(=[O:72])=[O:71]>>[F:29][C:27]1[CH:28]=[C:23]([NH:22][C:21]2[C:16]([C:11]3[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([NH2:8])[N:10]=3)=[CH:17][C:18]([CH:32]([N:37]3[CH2:38][CH2:39][N:40]([S:70]([CH3:69])(=[O:72])=[O:71])[CH2:41][CH2:42]3)[C:33]([F:34])([F:35])[F:36])=[CH:19][N:20]=2)[CH:24]=[N:25][C:26]=1[O:30][CH3:31]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 62406Trifluoromethanesulfonic acid

HCID 66612100HCID 66612100, compound

Product 1

HCID 49785919HCID 49785919, compound

Procedure

The title compound was prepared from tert-butyl 4-(1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-2,2,2-trifluoroethyl)piperazine-1-carboxylate via the similar deprotection step as previously described in Example 178, Step 4 using trifluoroacetic acid and trifluoromethanesulfonic acid and isolated (quantitative) as a yellow solid. m/z (ESI, +ve ion) 572 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.96 (s, 1H) 8.84 (d, J=2.15 Hz, 1H) 8.40 (d, J=2.35 Hz, 1H) 8.29-8.39 (m, 2H) 8.03 (br. s., 1H) 7.88 (br. s., 1H) 4.86 (q, J=9.45 Hz, 1H) 3.95 (s, 3H) 3.13 (t, J=4.60 Hz, 4H) 2.86 (s, 3H) 2.69-2.78 (m, 2H) 2.58-2.69 (m, 2H) 2.45 (s, 3H).

Workup

customisolated (quantitative) as a yellow solid

Sources & evidence

ORD record: ord-2c9f3dc19efd4d1eace9c9796d389171
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362241B2

Reaction notes

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