Diisopropylethylamine → HCID 58777633, compound

HRID 1435328Notes

Reaction equation

HRID 1435328 reaction equation
[F:1]C(F)(F)C(O)=O.[CH3:8][S:9]([N:12]1[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]1)(=[O:11])=[O:10].[NH2:19][C:20]1[C:25]([C:26]([C:28]2[C:36]3[O:35]C=C[C:32]=3[CH:31]=[C:30]([F:37])[CH:29]=2)=[O:27])=[CH:24][N:23]=[C:22](Cl)[N:21]=1.C(N(C(C)C)CC)(C)C>C(O)C>[NH2:19][C:20]1[C:25]([C:26]([C:28]2[C:36]([OH:35])=[CH:32][CH:31]=[C:30]([F:37])[C:29]=2[F:1])=[O:27])=[CH:24][N:23]=[C:22]([NH:18][CH:15]2[CH2:14][CH2:13][N:12]([S:9]([CH3:8])(=[O:11])=[O:10])[CH2:17][CH2:16]2)[N:21]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11975076[1-(Methylsulfonyl)piperidin-4-yl]amine trifluoroacetateHCID 21070552HCID 21070552, compound

Product 1

HCID 58777633HCID 58777633, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

trifluoroacetic acid salt (0.68 g, 2.3 mmol, Example 162), (4-amino-2-chloro-pyrimidin-5-yl)-(5-fluoro-benzofuran-7-yl)-methanone (0.5 g, 1.7 mmol, Step F), and diisopropylethylamine (1 mL, Aldrich) were combined with ethanol (20 mL) and refluxed for 12 hours. The reaction was cooled and diluted with ice water (˜60 mL). After 2 hours, the suspension was filtered and dried at 50° C. and high vacuum to give 0.35 g (57%) of [4-amino-2-(1-methanesulfonyl-piperidin-4-ylamino)-pyrimidin-5-yl]-(2,3-difluoro-6-hydroxy-phenyl)-methanone as a white solid. HRMS, observed: 434.1297; Calcd for (M+H)+: 434.1293. CDK4 IC50=0.030 μM; CDK1 IC50=0.058 μM; CDK2 IC50=0.002 μM; HCT 116 IC90=3.300 μM.

Workup

  1. temperaturerefluxed for 12 hours
  2. temperatureThe reaction was cooled
  3. filtrationthe suspension was filtered
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-2f47f70980e44200b7dcd22708b56403
Source dataset
uspto-grants-2009_11
Patent number
US07615634B2

Reaction notes

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