Water → HCID 67988083, compound

HRID 2168214Notes

Reaction equation

HRID 2168214 reaction equation
Cl[C:2]1[C:3]2[C:10]([Cl:11])=[CH:9][N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH:21]1[CH2:26][CH2:25][CH:24]([NH:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C.O>CN1C(=O)CCC1>[Cl:11][C:10]1[C:3]2[C:2]([N:21]3[CH2:26][CH2:25][CH:24]([NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:23][CH2:22]3)=[N:7][CH:6]=[N:5][C:4]=2[N:8]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 118120N-4-PiperidylbenzamideHCID 86710210HCID 86710210, compound

Product 1

HCID 67988083HCID 67988083, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4,5-dichloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine D40 (400 mg) and N-4-piperidinylbenzamide (300 mg, 1.46 mmol) were dissolved in NMP (4 ml), then N,N-diisopropylethylamine (315 mg, 2.44 mmol) was added dropwise. The reaction was stirred at room temperature for 16 hours then poured into water extracted with EtOAc (2×100 ml). Organic layer was washed with water (4×30 ml), brine (50 ml), dried with MgSO4, filtered and solvent removed. Yellow solid obtained was purified by flash chromatography on silica gel eluting with pet eth/ethyl acetate 3/1 to give the desired product D41 in 260 mg as a yellow solid. LCMS [MH+] [email protected] min (5 min run)

Workup

  1. extractionextracted with EtOAc (2×100 ml)
  2. washOrganic layer was washed with water (4×30 ml), brine (50 ml)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customsolvent removed
  6. customYellow solid obtained
  7. customwas purified by flash chromatography on silica gel eluting with pet

Sources & evidence

ORD record
ord-4a6f0f59449440758b59abaf473b16ea
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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