Trifluoroacetic acid → HCID 136266711, compound

HRID 526150Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]3[CH2:26][CH2:25][CH2:24][C@@H:23]([NH:27]C(=O)OC(C)(C)C)[CH2:22]3)=[N:19][CH:20]=1)=[N:11][C:10]([C:35]1[CH:40]=[C:39]([Cl:41])[C:38]([OH:42])=[C:37]([Cl:43])[CH:36]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>>[ClH:41].[ClH:41].[ClH:41].[NH2:27][C@@H:23]1[CH2:24][CH2:25][CH2:26][N:21]([C:18]2[N:19]=[CH:20][C:15]([NH:14][C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[C:10]([C:35]5[CH:36]=[C:37]([Cl:43])[C:38]([OH:42])=[C:39]([Cl:41])[CH:40]=5)[N:11]=4)[N:6]=[CH:5][C:4]=3[C:1](=[O:3])[CH3:2])=[CH:16][CH:17]=2)[CH2:22]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 136927346(R)-tert-butyl 1-(5-(3-acetyl-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-4-ylamino)pyridin-2-yl)piperidin-3-ylcarbamate

Product 1

HCID 136266711HCID 136266711, compoundYield 233.9%

Procedure

Following general procedure IV-2, (R)-tert-butyl 1-(5-(3-acetyl-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-4-ylamino)pyridin-2-yl)piperidin-3-ylcarbamate (60 mg, 0.10 mmol) was reacted with TFA (1.5 mL) to afford the desired product (37 mg, 74%) as a yellow-brown solid: 1H NMR (500 MHz, CD3OD) δ 9.28 (s, 1H), 8.49-8.31 (m, 2H), 8.16 (d, J=2.7 Hz, 1H), 7.63 (dd, J=9.1, 2.8 Hz, 1H), 7.51 (s, 2H), 6.98 (d, J=9.1 Hz, 1H), 4.40 (dd, J=12.7, 3.6 Hz, 1H), 3.93 (d, J=13.4 Hz, 1H), 3.41-3.19 (m, 3H), 2.80 (s, 3H), 2.16 (m, 1H), 1.97-1.89 (m, 1H), 1.78-1.65 (m, 2H); ESI MS m/z 523 [M+H]+; HPLC 98.1% (AUC), tR=9.87 min.

Sources & evidence

ORD record: ord-d50affc61e574167a7c3cdc21fe29ec6
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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