2-Morpholinoethylamine → 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl N-(2-morpholinoethyl)carbamate

HRID 51516Notes

Reaction equation

HRID 51516 reaction equation
[C:1](=[O:41])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH:3]1[CH2:7][CH2:6][CH:5]([N:8]2[C:12]3[N:13]=[CH:14][N:15]=[C:16]([NH2:17])[C:11]=3[C:10]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)=[CH:9]2)[CH2:4]1.[O:42]1[CH2:47][CH2:46][N:45]([CH2:48][CH2:49][NH2:50])[CH2:44][CH2:43]1>ClCCl.C(OCC)(=O)C>[O:42]1[CH2:47][CH2:46][N:45]([CH2:48][CH2:49][NH:50][C:1](=[O:41])[O:2][CH:3]2[CH2:7][CH2:6][CH:5]([N:8]3[C:12]4[N:13]=[CH:14][N:15]=[C:16]([NH2:17])[C:11]=4[C:10]([C:18]4[CH:19]=[CH:20][C:21]([O:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[CH:22][CH:23]=4)=[CH:9]3)[CH2:4]2)[CH2:44][CH2:43]1

Participants

5

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 865890083-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl (4-nitrophenyl) carbonate

Product 1

HCID 227362693-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl N-(2-morpholinoethyl)carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[4-Amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl (4-nitrophenyl) carbonate (0.052 mmol) in dichloromethane (1 ml) was added to 2-morpholinoethylamine (0.2 ml). The resulting mixture was stirred under nitrogen at ambient temperature for 24 hours. The reaction mixture was diluted with ethyl acetate and washed, dried (MgSO4), filtered and evaporated. The solid was purified by preparative HPLC to give 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl N-(2-morpholinoethyl)carbamate. The structure was confirmed by 1H NMR and LC/MS (MH+=543).

Workup

  1. washwashed
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe solid was purified by preparative HPLC

Sources & evidence

ORD record
ord-cc1bc1fae08b4d8aadddb61f585bbd77
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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