Diisopropylethylamine → HCID 58346320, compound

HRID 2096374Notes

Reaction equation

HRID 2096374 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.Cl[C:21]1[N:26]=[CH:25][N:24]=[C:23]([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:30]=2[F:36])=[O:28])[CH:22]=1.CCN(C(C)C)C(C)C>CS(C)=O>[F:36][C:30]1[C:31]([F:35])=[CH:32][CH:33]=[CH:34][C:29]=1[C:27]([C:23]1[N:24]=[CH:25][N:26]=[C:21]([NH:1][C:2]2[CH:3]=[C:4]3[C:17](=[CH:18][CH:19]=2)[CH2:16][C:6]2([C:14]4[C:9](=[N:10][CH:11]=[CH:12][CH:13]=4)[NH:8][C:7]2=[O:15])[CH2:5]3)[CH:22]=1)=[O:28]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58346324HCID 58346324, compoundHCID 591667225-amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 58346320HCID 58346320, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

70 mg (0.28 mmol) 5-amino-1,3-dihydrospiro[inden-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, 80 mg (0.28 mmol) (6-chloro-pyrimidin-4-yl)-(2.3-difluoro-phenyl)-methanone and 60 μL DIPEA in 600 μL dimethylsulphoxide were stirred for 1 h at 80° C. After cooling the reaction mixture was combined with approx. 10 mL ice water. The liquid was decanted off and the residue was dissolved in DCM and MeOH. After drying with sodium sulphate the mixture was filtered and the solvent was evaporated down. The residue was triturated with ether, suction filtered and dried.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customThe liquid was decanted off
  3. dissolutionthe residue was dissolved in DCM
  4. dry with materialAfter drying with sodium sulphate the mixture
  5. filtrationwas filtered
  6. customthe solvent was evaporated down
  7. customThe residue was triturated with ether, suction
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-aa487a3126074c02a38ec6281568a2d0
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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