Hydrochloric Acid → HCID 16041044, compound

HRID 545194Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:30](=[CH:31][CH:32]=1)[O:29][C:7]1([CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]4[C:17](=[C:18]([O:27][CH3:28])[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[O:14])[CH2:9][CH2:8]1)[CH2:6][C:5]2=[O:33].[Cl:34][C:35]([O:37][CH3:38])=[O:36].CC(OC(C)=O)=O.Cl>>[ClH:34].[CH3:26][O:25][C:23]1[C:22]2[C:17](=[C:18]([O:27][CH3:28])[CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:13]([N:10]2[CH2:11][CH2:12][C:7]3([CH2:6][C:5](=[O:33])[C:4]4[C:30](=[CH:31][CH:32]=[C:2]([NH:1][C:35]([O:37][CH3:38])=[O:36])[CH:3]=4)[O:29]3)[CH2:8][CH2:9]2)=[O:14])[CH:24]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 6586Methyl chloroformate

HCID 7918Acetic Anhydride

HCID 16041579HCID 16041579, compound

Product 1

HCID 16041044HCID 16041044, compound

Procedure

The free form of the compound was prepared according to the procedure described in Example 30 but using 6-amino-1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]spiro[chroman-2,4′-piperidin]-4-one and methyl chloroformate instead of 6-(piperazin-1-yl)-1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]spiro[chroman-2,4′-piperidin]-4-one and Ac2O. Then the material was converted to HCl salt according to the procedure described in Example 2. 1H-NMR (400 MHz, DMSO-d6) δ: 9.65 (1H, s), 7.84 (1H, s), 7.73-7.53 (3H, m), 7.36-7.25 (2H, m), 7.06 (1H, d, J=9.0 Hz), 4.34-4.18 (1H, m), 4.10 (3H, s), 3.97 (3H, s), 3.69-3.26 (3H, m), 3.64 (3H, s), 2.86 (2H, s), 2.10-1.71 (4H, m). MS [M+H]+=506.

Workup

customThe free form of the compound was prepared

Sources & evidence

ORD record: ord-d86126a05dee4606bb48fc7eafb02f4c
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935712B2

Reaction notes

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