Pyrrolidine → HCID 59361966, compound

HRID 61654Notes

Reaction equation

HRID 61654 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[C:10]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:32])[CH2:25][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:18]=1)[N:9]=[C:8]2[NH:33][C:34]1[CH:35]=[C:36]2[C:40](=[CH:41][CH:42]=1)[N:39]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[N:38]=[CH:37]2.[NH:50]1[CH2:54][CH2:53][CH2:52][CH2:51]1>CN(C=O)C.C1COCC1>[CH3:16][O:15][C:14]1[CH:13]=[C:12]2[C:7]([C:8]([NH:33][C:34]3[CH:35]=[C:36]4[C:40](=[CH:41][CH:42]=3)[N:39]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[N:38]=[CH:37]4)=[N:9][C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][C:24](=[O:32])[CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:18]=3)=[N:11]2)=[CH:6][C:5]=1[O:4][CH2:3][CH2:2][N:50]1[CH2:54][CH2:53][CH2:52][CH2:51]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 59361983HCID 59361983, compound

Product 1

HCID 59361966HCID 59361966, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 5-(6-(2-chloroethoxy)-7-methoxy-2-(3-(2-morpholinoacetamido)phenyl)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.280 g, 0.407 mmol) in DMF (2 mL) and THF (3 mL) was added pyrrolidine (0.8 mL). The resultant mixture was heated at 85° C. for 2 h, upon which it was allowed to cool to RT, the volatiles were removed in vacuo and the residue was taken up in ice-water (200 mL). The resulting precipitate was collected via filtration and subjected to preparative TLC (SiO2, CH2Cl2:MeOH 83:17) to give tert-butyl 5-(7-methoxy-2-(3-(2-morpholinoacetamido)-phenyl)-6-(2-(pyrrolidin-1-yl)ethoxy)quinazolin-4-ylamino)-1H-indazole-1-carboxylate (0.085 g, 0.118 mmol, 29%). HPLC retention time 3.81 minutes.

Workup

  1. customthe volatiles were removed in vacuo
  2. filtrationThe resulting precipitate was collected via filtration

Sources & evidence

ORD record
ord-fd0f27e097b440daa994e63b7887b3d8
Source dataset
uspto-grants-2016_09
Patent number
US09440961B2

Reaction notes

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