Dichloromethane → N-(8-Morpholino-5-(6-(piperazin-1-yl)pyridin-3-yl)imidazo[1,2-a]pyrazin-2-yl)quinoline-2-carboxamide hydrochloric acid salt

HRID 1772638Notes

Reaction equation

HRID 1772638 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:32]=[C:33]([NH:35][C:36]([C:38]4[CH:47]=[CH:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]=4)=[O:37])[N:34]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([N:19]4[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]4)=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.C(Cl)[Cl:49]>C(O)(C(F)(F)F)=O.CO>[ClH:49].[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:32]=[C:33]([NH:35][C:36]([C:38]4[CH:47]=[CH:46][C:45]5[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=5)[N:39]=4)=[O:37])[N:34]=3)[C:10]([C:13]3[CH:18]=[N:17][C:16]([N:19]4[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]4)=[CH:15][CH:14]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 117732270tert-Butyl 4-(5-(8-morpholino-2-(quinoline-2-carboxamido)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 86345528N-(8-Morpholino-5-(6-(piperazin-1-yl)pyridin-3-yl)imidazo[1,2-a]pyrazin-2-yl)quinoline-2-carboxamide hydrochloric acid salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of compound 21d (170 mg, 0.26 mmol) in DCM (6.8 mL), TFA (2.2 mL) was added. The resulting mixture was stirred at rt for 1 h and concentrated under reduced pressure. The residue obtained was dissolved in MeOH (20 mL) and passed through a MeOH pre-washed Bio-Rad AG-2X8 Cl-exchange column (50 g). The eluent was concentrated and dried under reduced pressure to obtain the title compound 125. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 11.11 (s, 1H), 9.19 (br. s., 2H), 8.66 (d, J=8.2 Hz, 1H), 8.43 (d, J=2.3 Hz, 1H), 8.29 (d, J=8.6 Hz, 1H), 8.20 (d, J=8.6 Hz, 1H), 8.10-8.16 (m, 2H), 8.00 (dd, J=8.8, 2.5 Hz, 1H), 7.91-7.97 (m, 1H), 7.78 (t, J=8.0 Hz, 1H), 7.45 (s, 1H), 7.20 (d, J=9.0 Hz, 1H), 4.22 (d, J=3.9 Hz, 4H), 3.87-3.94 (m, 4H), 3.79-3.86 (m, 4H), 3.24 (none, 4H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H29N9O2: 536.2 (M+H). Found 536.3.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. concentrationThe eluent was concentrated
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-429153a675714cdab01398706510dbd1
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…