Trifluoroacetic acid → HCID 178487413, compound

HRID 2271733Notes

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@@H:17]2[CH2:22][CH2:21][C@H:20]([NH:23]C(=O)OC(C)(C)C)[CH2:19][CH2:18]2)=[CH:13][C:12]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([O:38][CH3:39])[CH:32]=2)=[CH:11][CH:10]=3)=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[NH2:23][C@@H:20]1[CH2:21][CH2:22][C@H:17]([NH:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([O:38][CH3:39])[CH:32]=4)[CH:13]=3)[N:8]=[CH:7][C:6]=2[C:4]([CH:1]2[CH2:2][CH2:3]2)=[O:5])[CH2:18][CH2:19]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 178487418HCID 178487418, compound

Product 1

HCID 178487413HCID 178487413, compoundYield 56%

Procedure

Following general procedure A-2, tert-butyl cis-4-[3-(cyclopropanecarbonyl)-6-(4-hydroxy-3-methoxyphenyl)quinolin-4-ylamino]cyclohexylcarbamate (43 mg, 0.100 mmol) was reacted with TFA (2 mL) to afford the desired product (20 mg, 56%) as a light yellow solid: 1H NMR (300 MHz, CD3OD) δ 9.26 (s, 1H), 8.39 (d, J=1.7 Hz, 1H), 8.10 (dd, J=8.8, 1.8 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.27 (d, J=2.1 Hz, 1H), 7.18 (dd, J=8.2, 2.1 Hz, 1H), 6.93 (d, J=8.2 Hz, 1H), 4.74 (s, 1H), 3.96 (s, 3H), 3.12-3.02 (m, 1H), 2.98-2.84 (m, 1H), 2.17 (d, J=9.9 Hz, 2H), 2.10-1.93 (m, 4H), 1.93-1.73 (m, 2H), 1.31-1.20 (m, 2H), 1.16-1.08 (m, 2H); ESI MS m/z 432 [C26H29N3O3+H]+; HPLC 98.4% (AUC), tR=9.93 min.

Sources & evidence

ORD record: ord-e26cc531f0bb494b95bc9197f4ba5327
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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