Diisopropylethylamine → HCID 118214760, compound

HRID 2205624Notes

Reaction equation

HRID 2205624 reaction equation
[NH2:1][C@H:2]([C:4]1[N:9]=[C:8]2[CH:10]=[CH:11][N:12]([CH3:13])[C:7]2=[CH:6][C:5]=1[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[CH3:3].[NH2:28][C:29]1[N:34]=[C:33](Cl)[C:32]([C:36]#[N:37])=[C:31]([CH3:38])[N:30]=1.CCN(C(C)C)C(C)C>CC(O)=O.C(#N)C>[NH2:28][C:29]1[N:34]=[C:33]([NH:1][C@H:2]([C:4]2[N:9]=[C:8]3[CH:10]=[CH:11][N:12]([CH3:13])[C:7]3=[CH:6][C:5]=2[NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:17][CH2:16]2)[CH3:3])[C:32]([C:36]#[N:37])=[C:31]([CH3:38])[N:30]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 754124462-Amino-4-chloro-6-methyl-5-pyrimidinecarbonitrileHCID 118214761HCID 118214761, compound

Product 1

HCID 118214760HCID 118214760, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

To crude tert-butyl (S)-4-((5-(1-aminoethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)amino)piperidine-1-carboxylate was added HOAc (2 drops), followed by ACN (2 mL), 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (0.083 g, 0.493 mmol), and DIPEA (0.344 mL, 1.970 mmol). The reaction mixture was stirred at 75° C. for 1 hour. LCMS showed the reaction was complete, though messy. The volatiles were removed by N2 flow. The crude title compound was used without further purification. ESI-MS m/z [M+H]+ calc'd for C26H35N9O2, 506. found 506.

Workup

  1. customThe volatiles were removed by N2 flow
  2. customThe crude title compound was used without further purification

Sources & evidence

ORD record
ord-2437996c2afe498ea11bb6a6078700d4
Source dataset
uspto-grants-2016_06
Patent number
US09371321B2

Reaction notes

Loading…