Diisopropylethylamine → HCID 86710205, compound

HRID 2168201Notes

Reaction equation

HRID 2168201 reaction equation
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:3]=1.C[N:22]([CH:30]1CCNC[CH2:31]1)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C([N:39]([CH2:43][CH3:44])[CH:40]([CH3:42])C)(C)C>>[Br:1][C:2]1[C:10]2[C:9]([N:39]3[CH2:40][CH2:42][CH:31]([CH2:30][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:44][CH2:43]3)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:3]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 224845355-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

Product 1

HCID 86710205HCID 86710205, compound

Procedure

A mixture of 5-bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine D5 (1.5 g), 1,1-dimethylethyl methyl(4-piperidinyl)carbamate (1.294 g, 6.04 mmol, commercially available from e.g Fluorochem, Apollo, or Astatech) and N,N-diisopropylethylamine (1.758 mL, 10.06 mmol) was heated at 150° C. for 20 min. Crude product needs to be purified by silica chromatography eluting with 10-50% EtOAc in isohexane. The fractions have been collected and the solvent has been evaporated to give the product D24 in 0.763 g. LC/MS [M+H]+549.71/[email protected] min (2 min run)

Workup

  1. customto be purified by silica chromatography
  2. washeluting with 10-50% EtOAc in isohexane
  3. customThe fractions have been collected
  4. customthe solvent has been evaporated
  5. customto give the product
  6. custom[email protected] min (2 min run)

Sources & evidence

ORD record
ord-904cf68b4cb24068ae5af1ce886ab60b
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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