Trifluoroacetic acid → HCID 66715465, compound

HRID 2271849Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C:15]1[CH:16]=[N:17][C:18]([N:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[N:19][CH:20]=1)=[CH:11][C:10]([C:34]1[CH:39]=[C:38]([F:40])[C:37]([OH:41])=[C:36]([Cl:42])[CH:35]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>>[Cl:42][C:36]1[CH:35]=[C:34]([C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[N:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[C:13]3[NH:14][C:15]2[CH:20]=[N:19][C:18]([N:21]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]3)=[N:17][CH:16]=2)[CH:39]=[C:38]([F:40])[C:37]=1[OH:41]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 68091863HCID 68091863, compound

Product 1

HCID 66715465HCID 66715465, compoundYield 26.6%

Procedure

Following procedure A-2 tert-butyl 4-(5-(3-acetyl-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-4-ylamino)pyrimidin-2-yl)piperazine-1-carboxylate (50 mg, 0.084 mmol) was treated with TFA (2 mL) to afford the desired product (11 mg, 26%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.29 (s, 1H), 8.55 (s, 2H), 8.23 (dd, J=11, 2 Hz, 1H), 8.02 (m, 2H), 7.12 (m, 2H), 4.21 (t, J=10 Hz, 4H), 3.35 (t, J=10.5 Hz, 4H) 2.80 (s, 3H); ESI MS m/z 493, [C25H22ClFN6O2+H]+; HPLC 99.0% (AUC), tR=9.90 min.

Sources & evidence

ORD record: ord-afd3f83de7904fe28ec3915e26b41327
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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