Hydrochloric Acid → 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl 2-aminoacetate hydrochloride

HRID 51513Notes

Reaction equation

HRID 51513 reaction equation
C(OC([NH:8][CH2:9][C:10]([O:12][CH:13]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[N:23]=[CH:24][N:25]=[C:26]([NH2:27])[C:21]=3[C:20]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:30][CH:29]=3)=[CH:19]2)[CH2:14]1)=[O:11])=O)(C)(C)C.[ClH:41].C(OCC)C>C(OCC)(=O)C>[ClH:41].[NH2:8][CH2:9][C:10]([O:12][CH:13]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[N:23]=[CH:24][N:25]=[C:26]([NH2:27])[C:21]=3[C:20]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:30][CH:29]=3)=[CH:19]2)[CH2:14]1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 227364343-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl 2-[(tert-butoxycarbonyl)amino]acetate

Product 1

HCID 227361863-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl 2-aminoacetate hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-[4-Amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl 2-[(tert-butoxycarbonyl)amino]acetate (39 mg, 0.072 mmol) was dissolved in ethyl acetate (2.5 ml). Hydrogen chloride gas was passed through for 1 minute. The flask was capped and the solution stirred for additional 30 minutes. Diethyl ether was added and precipitate formed. The solid was collected by filtration to give 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl 2-aminoacetate hydrochloride. The structure was confirmed by 1H NMR and LC/MS (MH+=444).

Workup

  1. customwas passed through for 1 minute
  2. customThe flask was capped
  3. customprecipitate formed
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-46378615f60640858a0eda9cafb3fe72
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Reaction notes

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