Trifluoroacetic acid → HCID 178467121, compound

HRID 2178852Notes

Reaction equation

C(OC(=O)[NH:7][CH:8]([CH:41]([CH3:43])[CH3:42])[C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:29]4[CH:34]=[C:33]([F:35])[C:32]([OH:36])=[C:31]([Cl:37])[CH:30]=4)[N:27]=3)[N:22]=[CH:21][C:20]=2[C:38](=[O:40])[CH3:39])[CH2:14][CH2:13]1)=[O:10])(C)(C)C.C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:64].Cl>>[ClH:37].[ClH:64].[C:38]([C:20]1[CH:21]=[N:22][C:23]2[C:28]([C:19]=1[NH:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([NH:11][C:9](=[O:10])[CH:8]([NH2:7])[CH:41]([CH3:43])[CH3:42])[CH2:13][CH2:14]1)=[N:27][C:26]([C:29]1[CH:34]=[C:33]([F:35])[C:32]([OH:36])=[C:31]([Cl:37])[CH:30]=1)=[CH:25][CH:24]=2)(=[O:40])[CH3:39]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

HCID 178467122HCID 178467122, compound

Product 1

HCID 178467121HCID 178467121, compoundYield 30%

Procedure

Following general procedure IV-2, tert-butyl[1-(trans-4-{[3-acetyl-6-(3-chloro-5-fluoro-4-hydroxyphenyl)-1,5-naphthyridin-4-yl]amino}cyclohexylamino)-3-methyl-1-oxobutan-2-yl]carbamate (0.19 mmol) was reacted with TFA (2 mL) followed by formation of the dihydrochloride salt to afford the desired product (35 mg, 30% over two steps) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.44 (d, J=9.0 Hz, 1H), 8.33 (d, J=9.0 Hz, 1H), 8.00 (s, 1H), 7.87 (dd, J=11.4, 2.2 Hz, 1H), 5.63-5.57 (m, 1H), 3.88-3.83 (m, 1H), 3.62 (d, J=6.0 Hz, 1H), 2.76 (s, 3H), 2.51-2.40 (m, 2H), 2.10-2.12 (m, 3H), 1.81-1.53 (m, 4H), 1.08 (t, J=7.4 Hz, 6H); ESI MS m/z 528 [M+H]+; HPLC 98.9% (AUC), tR=9.99 min.

Sources & evidence

ORD record: ord-ced233d368214e21a81a19a3b04d2888
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067937B2

Reaction notes

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