Trifluoroacetic acid → HCID 178467121, compound

HRID 526131Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:35])[CH:23]([NH:27]C(=O)OC(C)(C)C)[CH:24]([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=[N:11][C:10]([C:36]1[CH:41]=[C:40]([F:42])[C:39]([OH:43])=[C:38]([Cl:44])[CH:37]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:64].Cl>>[ClH:44].[ClH:64].[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:35])[CH:23]([NH2:27])[CH:24]([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=[N:11][C:10]([C:36]1[CH:41]=[C:40]([F:42])[C:39]([OH:43])=[C:38]([Cl:44])[CH:37]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2]

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-a995ede6fc99484bbae65519de6f71a4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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