Ethylenediamine → HCID 117683826, compound

HRID 1507549Notes

Reaction equation

HRID 1507549 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([C:11]3[C:12]([NH:25][C@@H:26]4[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27]4)=[N:13][C:14]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:15][C:16]=3[O:17][CH3:18])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:39]([NH2:42])[CH2:40][NH2:41].CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[NH2:41][CH2:40][CH2:39][NH:42][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[C:12]([NH:25][C@@H:26]4[CH2:31][CH2:30][CH2:29][N:28]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27]4)=[N:13][C:14]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[N:15][C:16]=3[O:17][CH3:18])[S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 23676156Sodium t-butoxideHCID 117683821HCID 117683821, compound

Product 1

HCID 117683826HCID 117683826, compound

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Into a mixture of tert-butyl (3R)-3-[[5-(4-chloro-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (150 mg, 0.25 mmol, 1.00 equiv), ethane-1,2-diamine (48.0 mg, 0.80 mmol, 3.00 equiv), sodium 2-methylpropan-2-olate (52.0 mg, 0.54 mmol, 2.00 equiv) and o-biphenyl(t-Bu)2P (10.7 mg, 0.04 mmol, 0.12 equiv) in toluene (6.0 mL) was added tris(dibenzylideneacetone) dipalladium (30.0 mg, 0.03 mmol, 0.10 equiv) and nitrogen was bubbled in for 5 min. The resulting mixture was heated for 12 h at 90° C. in an oil bath. After removed the solvent, the residue was purified by flash chromatography on silica gel, eluting with a mixture of 10% MeOH in CH2Cl2 to give the title compound as a yellow solid. MS m/z [M+H]+ (ESI): 585.

Workup

  1. customwas bubbled in for 5 min
  2. customAfter removed the solvent
  3. customthe residue was purified by flash chromatography on silica gel
  4. washeluting with a mixture of 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-eeeba93487734aa18f7399d41436bd94
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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