Trifluoroacetic acid → HCID 66716279, compound

HRID 2271798Notes

Reaction equation

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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86692945HCID 86692945, compound

Product 1

HCID 66716279HCID 66716279, compoundYield 14%

Procedure

Following general procedure A-2, tert-butyl 4-(5-((3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-yl)amino)pyrimidin-2-yl)piperazine-1-carboxylate (0.10 mmol) was reacted with TFA (2 mL) to afford the desired product (7.4 mg, 14% over two steps) as a yellow solid. 1H NMR (500 MHz, MeOD) δ 9.24 (s, 1H), 8.30 (s, 2H), 7.93 (d, J=1.3 Hz, 2H), 7.83 (d, J=1.3 Hz, 1H), 7.21 (s, 2H), 3.98 (t, J=5.2 Hz, 4H), 3.06 (t, J=5.2 Hz, 4H), 2.94-2.86 (m, 1H), 1.24-1.08 (m, 4H). ESI MS m/z 535 [C27H24Cl2N6O2+H]+; HPLC>99% (AUC), tR=11.54 min.

Sources & evidence

ORD record: ord-1aeba3dd478549bb9769518b041dd162
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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