Trifluoroacetic acid → HCID 66716517, compound

HRID 2271951Notes

Reaction equation

[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)=[N:21][CH:22]=1)=[CH:13][C:12]([C:36]1[CH:41]=[C:40]([F:42])[C:39]([OH:43])=[C:38]([Cl:44])[CH:37]=1)=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O>>[Cl:44][C:38]1[CH:37]=[C:36]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[C:15]3[NH:16][C:17]2[CH:22]=[N:21][C:20]([N:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)=[CH:19][CH:18]=2)[CH:41]=[C:40]([F:42])[C:39]=1[OH:43]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86692990HCID 86692990, compound

Product 1

HCID 66716517HCID 66716517, compoundYield 52.1%

Procedure

Following general procedure A-2, tert-butyl 4-{5-[3-butyryl-6-(3-chloro-5-fluoro-4-hydroxyphenyl)quinolin-4-ylamino]pyridin-2-yl}piperazine-1-carboxylate (0.144 mmol) was reacted with TFA (2 mL) to afford the desired product (39 mg, 51% over two steps) as a yellow solid: 1H NMR (500 MHz, CD3OD+TFA-d) δ 9.29 (s, 1H), 8.29 (d, J=2.7 Hz, 1H), 8.20 (dd, J=8.8, 2.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.74 (dd, J=8.8, 2.7 Hz, 1H), 7.16 (d, J=9.0 Hz, 1H), 7.11-7.02 (m, 2H), 3.94 (t, J=5.3 Hz, 4H), 3.37 (t, J=5.3 Hz, 4H), 3.19 (t, J=7.2 Hz, 2H), 1.87-1.76 (m, 2H), 1.11-1.04 (t, J=7.2 Hz, 3H); ESI MS m/z 520 [C28H27ClFN5O2+H]+; HPLC>99% (AUC), tR=10.99 min.

Sources & evidence

ORD record: ord-fb3443a86d1148a386e09e6f2307448e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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