Azetidine → HCID 71730633, compound

HRID 1056225Notes

Reaction equation

HRID 1056225 reaction equation
[C:1]([NH:5][C:6]1[C:7](Cl)=[N:8][C:9]2[C:14]([N:15]=1)=[C:13]([C:16]1[NH:24][C:23]3[CH2:22][CH2:21][NH:20][C:19](=[O:25])[C:18]=3[CH:17]=1)[CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2].[NH:27]1[CH2:30][CH2:29][CH2:28]1.CCN(C(C)C)C(C)C>CS(C)=O>[N:27]1([C:7]2[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[C:16]3[NH:24][C:23]4[CH2:22][CH2:21][NH:20][C:19](=[O:25])[C:18]=4[CH:17]=3)[N:8]=2)[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 71730509HCID 71730509, compound

Product 1

HCID 71730633HCID 71730633, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

This compound (18 mg, 61% yield) as a yellow solid was prepared according to the procedures described for Example 346, using 2-(3-(tert-butylamino)-2-chloroquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (345) (28 mg, 0.076 mmol), azetidine (25.5 pt, 0.37 mmol, Matrix Scientific, Columbia, S.C.), and DIEA (26.4 μL, 0.15 mmol) in DMSO (0.75 mL) at 50° C. for 1 h. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53 (s, 9H) 2.30 (quin, J=7.58 Hz, 2H) 2.85 (t, J=6.85 Hz, 2H) 3.43 (td, J=6.85, 2.35 Hz, 2H) 4.22 (t, J=7.63 Hz, 4H) 5.68 (s, 1H) 6.95 (s, 1H) 6.95 (s, 1H) 7.23 (t, J=7.82 Hz, 1H) 7.35 (dd, J=8.02, 1.37 Hz, 1H) 7.60 (dd, J=7.43, 1.37 Hz, 1H) 12.01 (br. s., 1H). MS (ESI, pos. ion) m/z: 391.2 (M+1).

Workup

  1. customat 50° C.
  2. customfor 1 h

Sources & evidence

ORD record
ord-2d582f796992434a9e2c387a1145950c
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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