Trifluoroacetic acid → HCID 66715662, compound

HRID 2271938Notes

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]=[CH: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:22]=[N:21][C:20]([N:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=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 86692984HCID 86692984, compound

Product 1

HCID 66715662HCID 66715662, compoundYield 41.2%

Procedure

Following general procedure A-2, tert-butyl 4-{5-[3-(cyclopropanecarbonyl)-6-(3,5-dichloro-4-hydroxyphenyl)quinolin-4-ylamino]pyridin-2-yl}piperazine-1-carboxylate (0.118 mmol) was reacted with TFA (2 mL) to afford the desired product (26 mg, 41% over two steps) as an orange solid: 1H NMR (300 MHz, CDCl3) δ 11.92 (s, 1H), 9.35 (s, 1H), 8.07-7.94 (m, 2H), 7.75-7.68 (m, 2H), 7.08-7.02 (m, 2H), 6.72-6.65 (m, 1H), 3.71-3.64 (m, 4H), 3.17-3.10 (m, 4H), 2.84-2.77 (m, 1H), 1.34-1.10 (m, 4H); ESI MS m/z 534 [C28H25Cl2N5O2+H]+; HPLC 97.3% (AUC), tR=8.65 min.

Sources & evidence

ORD record: ord-873ce907a3784af6b760891d4e703373
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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