4-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid → 1-{4-[4-Amino-2-(3,4-dichlorophenyl)-butyryl]-piperazin-1-yl}-quinolizin-4-one hydrochloride

HRID 1192390Notes

Reaction equation

HRID 1192390 reaction equation
[N:1]1([CH:7]2[CH:16]3[N:11]([CH:12]=[CH:13][CH:14]=[CH:15]3)[C:10](=[O:17])[CH:9]=[CH:8]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(OC([NH:25][CH2:26][CH2:27][CH:28]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)[C:29](O)=[O:30])=O)(C)(C)C>>[ClH:38].[NH2:25][CH2:26][CH2:27][CH:28]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)[C:29]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10](=[O:17])[N:11]3[C:16]=2[CH:15]=[CH:14][CH:13]=[CH:12]3)[CH2:2][CH2:3]1)=[O:30]

Participants

3

Reactant 2

HCID 221479534-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acidHCID 675397771-Piperazin-1-yl-1,9a-dihydro-quinolizin-4-one

Product 1

HCID 865987341-{4-[4-Amino-2-(3,4-dichlorophenyl)-butyryl]-piperazin-1-yl}-quinolizin-4-one hydrochloride

Procedure

1-{4-[4-Amino-2-(3,4-dichlorophenyl)-butyryl]-piperazin-1-yl}-quinolizin-4-one hydrochloride was prepared by substituting 5-piperazin-1-yl-1H-indazole with 1-Piperazin-1-yl-1,9a-dihydro-quinolizin-4-one and substituting (D)-Boc-4-chlorophenylalanine with 4-tert-Butoxycarbonylamino-2-(3,4-dichlorophenyl)-butyric acid in Example 34, Step 2, then removing the Boc protecting group as described in Example 34, Step 3. 1H NMR (CD3OD, 400 MHz) δ 9.25 (d, J=7.2 Hz, 1H), 9.57 (d, J=8.8 Hz, 1H), 8.00 (m, 2H), 7.71 (d, J=7.2 Hz, 1H), 7.58 (m, 2H), 7.33 (d, J=8.0 Hz, 1H), 7.02 (d, J=8.4 Hz, 1H), 4.31 (m, 1H), 3.82 (m, 5H), 3.65 (m, 2H), 3.34 (m, 1H), 2.98 (m, 1H), 2.86 (m, 1H), 2.36 (m, 1H), 2.03 (m, 1H). LCMS (APCI+) m/z 459, 461, 463 [M+H]+; Rt=2.02 min.

Workup

  1. customremoving the Boc protecting group

Sources & evidence

ORD record
ord-b69adf22f2834722aa5c362ff3afa86f
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

Loading…