Hydrochloric Acid → HCID 178467100, compound

HRID 526137Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:35])[CH:23]([NH:27]C(=O)OC(C)(C)C)[CH:24]([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=[N:11][C:10]([C:36]1[CH:41]=[C:40]([Cl:42])[C:39]([OH:43])=[C:38]([Cl:44])[CH:37]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[ClH:45]>>[ClH:42].[ClH:45].[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:35])[CH:23]([NH2:27])[CH:24]([CH3:26])[CH3:25])[CH2:17][CH2:16]1)=[N:11][C:10]([C:36]1[CH:37]=[C:38]([Cl:44])[C:39]([OH:43])=[C:40]([Cl:42])[CH:41]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 136927280HCID 136927280, compound

Product 1

HCID 178467100HCID 178467100, compoundYield 47%

Procedure

Following general procedure IV-2, tert-butyl 1-(4-(3-acetyl-6-(3,5-dichloro-4-hydroxy-phenyl)-1,5-naphthyridin-4-ylamino)cyclohexylamino)-3-methyl-1-oxobutan-2-ylcarbamate (0.19 mmol) was reacted with HCl (5 mL, 2 M in ether) to afford the desired product (55 mg, 47% over two steps) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.45 (d, J=9.0 Hz, 1H), 8.33 (d, J=9.0 Hz, 1H), 8.10 (s, 2H), 5.67-5.53 (m, 1H), 3.91-3.80 (m, 1H), 3.62 (d, J=6.0 Hz, 1H), 2.76 (s, 3H), 2.49-2.40 (m, 2H), 2.25-2.10 (m, 3H), 1.81-1.54 (m, 4H), 1.07 (dd, J=9.0, 6.9 Hz, 6H); ESI MS m/z 544 [M+H]+; HPLC 99.0% (AUC), tR=10.15 min.

Sources & evidence

ORD record: ord-054bd15055a047e7a7247da48ed993d7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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