Hydrochloric Acid → HCID 11339067, compound

HRID 1765553Notes

Reaction equation

HRID 1765553 reaction equation
Cl.Cl.FC1C=C2C(=CC=1)NC=C2CCCNC1COC2C(=C3C(=CC=2)N=CC=C3)C1.Cl.Cl.CCOCC.Cl.Cl.[F:40][C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[NH:46][CH:45]=[C:44]2[CH2:50][CH2:51][CH2:52][N:53]([CH2:68][CH2:69][CH3:70])[CH:54]1[CH2:67][O:66][C:65]2[C:56](=[C:57]3[C:62](=[CH:63][CH:64]=2)[N:61]=[CH:60][CH:59]=[CH:58]3)[CH2:55]1>C(OCC)(=O)C.CS(C)=O>[F:40][C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[NH:46][CH:45]=[C:44]2[CH2:50][CH2:51][CH2:52][N:53]([CH2:68][CH2:69][CH3:70])[CH:54]1[CH2:67][O:66][C:65]2[C:56](=[C:57]3[C:62](=[CH:63][CH:64]=2)[N:61]=[CH:60][CH:59]=[CH:58]3)[CH2:55]1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 10953452Ether hydrochlorideHCID 69497606HCID 69497606, compoundHCID 69497608HCID 69497608, compound

Product 1

HCID 11339067HCID 11339067, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared generally following the procedure above for example 22 using (−)-N-[3-(5-fluoro-1H-indol-3-yl)propyl]-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine (example 21b) as starting material. It was converted to the HCl salt by dissolution in ethyl acetate and addition of 1M HCl/Et2O (2.4 eq) to generate (+)-N-[3-(5-fluoro-1H-indol-3-yl)propyl]-N-propyl-2,3-dihydro-1H-pyrano[3,2-f]quinolin-2-amine bis-hydrochloride salt as a yellow solid: mp 106° C./dec. [α]D25=+38.0° (c=1% solution, DMSO). MS ESI m/z 418 [M+H]+. Elemental Analysis for C26H28FN3O·2.00 HCl; Calculated: C, 63.67; H, 6.17; N, 8.57. Found: C, 63.32; H, 6.39; N, 8.27.

Workup

  1. customThis compound was prepared generally

Sources & evidence

ORD record
ord-51a7dd3490be41a08718845fc1554903
Source dataset
uspto-grants-2007_06
Patent number
US07227023B2

Reaction notes

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