Trifluoroacetic acid → HCID 178487414, compound

HRID 2271712Notes

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 178487419HCID 178487419, compound

Product 1

HCID 178487414HCID 178487414, compoundYield 31%

Procedure

Following general procedure A-2, tert-butyl trans-4-[3-(cyclopropanecarbonyl)-6-(4-hydroxy-3-methoxyphenyl)quinolin-4-ylamino]cyclohexylcarbamate (45 mg, 0.085 mmol) was reacted with TFA (2 mL) to afford the desired product (11.3 mg, 31%) as a yellow solid: 1H NMR (500 MHz, CD3OD) δ 9.12 (s, 1H), 8.36 (s, 1H), 8.04-7.98 (m, 1H), 7.89 (d, J=8.7 Hz, 1H), 7.26 (d, J=1.9 Hz, 1H), 7.17 (dd, J=8.2, 2.0 Hz, 1H), 6.93 (d, J=8.2 Hz, 1H), 4.14 (s, 1H), 3.97 (s, 3H), 3.20-3.07 (m, 2H), 2.87-2.75 (m, 2H), 2.28 (d, J=12.2 Hz, 2H), 2.01 (d, J=11.6 Hz, 2H), 1.64-1.53 (m, 2H), 1.40-1.26 (m, 3H), 1.21-1.14 (m, 2H), 1.12-1.03 (m, 2H); ESI MS m/z 432 [C26H29N3O3+H]+; HPLC 98.8% (AUC), tR=7.95 min.

Sources & evidence

ORD record: ord-acfd00135a8b461cbd2199d852e3208f
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120749B2

Reaction notes

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