Trifluoroacetic acid → HCID 59548458, compound

HRID 1621915Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:16]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([N:24](CC4C=CC(OC)=CC=4)CC4C=CC(OC)=CC=4)[N:18]=3)=[CH:15][C:14]([CH2:43][N:44]3[CH2:49][CH2:48][N:47]([S:50]([CH3:53])(=[O:52])=[O:51])[CH2:46][C@H:45]3[CH3:54])=[CH:13][N:12]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9].FC(F)(F)C(O)=O.FC(F)(F)S(O)(=O)=O>>[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:16]([C:17]3[N:22]=[C:21]([CH3:23])[N:20]=[C:19]([NH2:24])[N:18]=3)=[CH:15][C:14]([CH2:43][N:44]3[CH2:49][CH2:48][N:47]([S:50]([CH3:53])(=[O:52])=[O:51])[CH2:46][C@H:45]3[CH3:54])=[CH:13][N:12]=2)[CH:5]=[N:6][C:7]=1[O:8][CH3:9]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 62406Trifluoromethanesulfonic acid

HCID 66611748HCID 66611748, compound

Product 1

HCID 59548458HCID 59548458, compound

Procedure

The title compound was prepared from (R)-4-(2-(5-fluoro-6-methoxypyridin-3-ylamino)-5-((2-methyl-4-(methylsulfonyl)piperazin-1-yl)methyl)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine via a similar deprotection step as previously described in Example 178, Step 4, using trifluoroacetic acid and trifluoromethanesulfonic acid, and isolated as a yellow solid. m/z (ESI, +ve ion) 518 (M+H)+. 1H NMR (400 MHz, d6-DMSO) δ 11.95 (s, 1H) 8.71 (d, J=2.35 Hz, 1H) 8.41 (d, J=2.15 Hz, 1H) 8.33-8.40 (m, 1H) 8.27 (d, J=2.15 Hz, 1H) 7.90 (br. s., 1H) 7.76 (br. s., 1H) 3.93 (s, 3H) 3.91 (s, 1H) 3.13-3.30 (m, 3H) 2.87-2.95 (m, 1H) 2.85 (s, 3H) 2.53-2.79 (m, 3H) 2.44 (s, 3H) 2.14-2.28 (m, 1H) 1.16 (d, J=6.26 Hz, 3H).

Workup

customisolated as a yellow solid

Sources & evidence

ORD record: ord-69a79fef227a4c3498dea7120ff05872
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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