Hydrochloric Acid → HCID 178467098, compound

HRID 526135Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:33])[CH:23]([NH:25]C(=O)OC(C)(C)C)[CH3:24])[CH2:17][CH2:16]1)=[N:11][C:10]([C:34]1[CH:39]=[C:38]([Cl:40])[C:37]([OH:41])=[C:36]([Cl:42])[CH:35]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[ClH:43]>>[ClH:40].[ClH:43].[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([NH:21][C:22](=[O:33])[CH:23]([NH2:25])[CH3:24])[CH2:17][CH2:16]1)=[N:11][C:10]([C:34]1[CH:35]=[C:36]([Cl:42])[C:37]([OH:41])=[C:38]([Cl:40])[CH:39]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 178467099HCID 178467099, compound

Product 1

HCID 178467098HCID 178467098, compoundYield 41%

Procedure

Following general procedure IV-1, crude tert-butyl 1-{trans-4-[3-acetyl-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-4-ylamino]cyclohexylamino}-1-oxopropan-2-ylcarbamate (0.13 mmol) was reacted with HCl (5 mL, 2 M in ether) to afford the desired product (32 mg, 41% over two steps) as a brown solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.45 (d, J=8.5 Hz, 1H), 8.34 (d, J=8.5 Hz, 1H), 8.10 (s, 2H), 5.65-5.55 (m, 1H), 3.90 (q, J=6.9 Hz, 1H), 3.85-3.76 (m, 1H), 2.76 (s, 3H), 2.50-2.39 (m, 2H), 2.21-2.10 (m, 2H), 1.78-1.69 (m, 2H), 1.65-1.52 (m, 2H), 1.51 (d, J=6.9 Hz, 3H); ESI MS m/z 516 [M+H]+; HPLC>99% (AUC), tR=9.65 min.

Sources & evidence

ORD record: ord-d2f8827731044fb2a130bd41701659b9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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