Dimethylamine → HCID 59168336, compound

HRID 2195085Notes

Reaction equation

HRID 2195085 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:35][CH:36]=O)[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[N:17]=[C:16]([N:28]3[CH2:32][CH2:31][CH2:30][C@H:29]3[CH3:33])[N:15]=2)[C@H:10]([CH3:34])[CH2:9]1.[CH3:38][NH:39][CH3:40]>ClCCCl.CC(O)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:35][CH2:36][N:39]([CH3:40])[CH3:38])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=3)[N:17]=[C:16]([N:28]3[CH2:32][CH2:31][CH2:30][C@H:29]3[CH3:33])[N:15]=2)[C@H:10]([CH3:34])[CH2:9]1

Participants

6

Reactant 2

HCID 674DimethylamineHCID 59168325HCID 59168325, compound

Product 1

HCID 59168336HCID 59168336, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-chloro-6-((R)-4-(6-(3-chloro-4-fluorophenyl)-2-((R)-2-methylpyrrolidin-1-yl)pyrimidin-4-yl)-3-methylpiperazin-1-yl)pyridin-3-yl)acetaldehyde (64 mg, 0.118 mmol) in DCE, add dimethylamine (3.87M in THF, 40 μL) followed by 1 drop of HOAc. Stir the mixture overnight, and then dilute with DCM and wash (2×) with 10% NaOH solution. Concentrate under reduced pressure and add EtOAc, followed by a solution of HCl in ether. Concentrate and triturate the hydrochloride salt with fresh EtOAc to afford the title compound. 1H NMR (400 MHz, CDCl3): δ1.31 (d, 3H, J=6.23 Hz, CH3), 1.39 (d, 3H, J=6.6 Hz, CH3), 1.68 (m, 1H), 1.91 (m, 1H), 2.05 (m, 5H), 2.68 (s, 6H, N(CH3)2), 2.9-3.1 (m, 4H), 3.65 (m, 1H), 3.63-3.9 (m, 4H), 4.34 (m, 2H), 4.67 (br s, 1H), 6.20 (s, 1H), 7.18 (t, 1H), 7.55 (s, 1H), 7.88 (m, 1H), 8.06 (s, 2H).

Workup

  1. washwash (2×) with 10% NaOH solution
  2. concentrationConcentrate under reduced pressure
  3. additionadd EtOAc
  4. concentrationConcentrate
  5. customtriturate the hydrochloride salt with fresh EtOAc

Sources & evidence

ORD record
ord-72364a4f7ba3455a948e54ede3676cb0
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

Loading…