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Hexahydro-1,4-diazepine → 5-Amino-2-[2-(4-fluorophenyl)ethyl]-7-(4-[2-(4-chlorophenoxy)acetyl]homopiperazin-1-yl)-thiazolo[5,4-d]pyrimidine

HRID 1507806
Notes
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Reaction equation

HRID 1507806 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](S(C)(=O)=O)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1.[NH:24]1[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(N(C(C)C)CC)(C)C.[Cl:40][C:41]1[CH:51]=[CH:50][C:44]([O:45][CH2:46][C:47](Cl)=[O:48])=[CH:43][CH:42]=1>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([N:24]2[CH2:30][CH2:29][CH2:28][N:27]([C:47](=[O:48])[CH2:46][O:45][C:44]3[CH:50]=[CH:51][C:41]([Cl:40])=[CH:42][CH:43]=3)[CH2:26][CH2:25]2)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 68163Hexahydro-1,4-diazepineHCID 77771p-Chlorophenoxyacetyl chlorideHCID 81531DiisopropylethylamineHCID 509418672-(4-Fluorophenethyl)-7-(methylsulfonyl)thiazolo[5,4-d]pyrimidin-5-amine

Product 1

HCID 469167595-Amino-2-[2-(4-fluorophenyl)ethyl]-7-(4-[2-(4-chlorophenoxy)acetyl]homopiperazin-1-yl)-thiazolo[5,4-d]pyrimidine
Yield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-amino-2-[2-(4-fluorophenyl)ethyl]-7-methanesulfonyl-thiazolo[5,4-d]pyrimidine (50 mg, 0.14 mmol) in dichloromethane (4 ml) was added homopiperazine (1.4 mmol). The reaction mixture was stirred at room temperature for 2 hours. The mixture was extracted, the organic phase was dried over MgSO4 after which the solvent was removed in vacuo. The residue was dissolved in dichloromethane whereupon diisopropylethylamine (0.28 mmol, 47 μL) followed by 4-chlorophenoxyacetyl chloride (0.14 mmol) were added. The reaction was stirred at room temperature for 24 hours after which the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 1% CH3OH in CH2Cl2), yielding the pure title compound (38 mg) which was characterized by its mass spectrum: MS m/z (%): 541 ([M+H]+, 100).

Workup

  1. extractionThe mixture was extracted
  2. dry with materialthe organic phase was dried over MgSO4 after which the solvent
  3. customwas removed in vacuo
  4. additionwere added
  5. stirringThe reaction was stirred at room temperature for 24 hours after which the solvent
  6. customwas removed in vacuo
  7. customThe resulting residue was purified by flash chromatography on silica
  8. additiona mixture of methanol and dichloromethane (in a ratio

Sources & evidence

ORD record
ord-69fbbfd65bfe4f90af9882ecc7c97a3c
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221822B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes