Cyclopropylamine → HCID 67219337, compound

HRID 916764Notes

Reaction equation

HRID 916764 reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C1([O:11][C:12](=O)[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([C:22]3[C:30]4[C:29]([NH2:31])=[N:28][CH:27]=[N:26][C:25]=4[N:24]([CH:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)[CH:23]=3)=[O:21])[CH:15]=2)C=CC=CC=1>C1COCC1>[NH2:31][C:29]1[C:30]2[C:22]([C:20]([C:16]3[CH:15]=[C:14]([NH:13][C:12]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:11])[CH:19]=[CH:18][CH:17]=3)=[O:21])=[CH:23][N:24]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:25]=2[N:26]=[CH:27][N:28]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 67219542HCID 67219542, compound

Product 1

HCID 67219337HCID 67219337, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropyl amine (130 mg, 2.3 mmol) was added to a solution of [3-(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-carbamic acid phenyl ester (50 mg, 0.11 mmol) in THF (3 mL). The reaction mixture was stirred at room temperature for 2 h and concentrated in vacuo. Purification by flash column chromatography (silica, 4:96→15:85 MeOH:CH2Cl2) provided the title compound as a pale yellow solid (44 mg, 95%). MS: 405.2 (MH+); HPLC Rf: 4.73 min. (HPLC method 4); HPLC purity: 100%.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by flash column chromatography (silica, 4:96→15:85 MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-1d40859c9fe843148e5ca76338eb3e3d
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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