Hydrochloric Acid → (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-[3-(3-amino-prop-1-ynyl)-phenyl]-methanone

HRID 916769Notes

Reaction equation

HRID 916769 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([C:20]2[C:28]3[C:27]([NH2:29])=[N:26][CH:25]=[N:24][C:23]=3[N:22]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:21]=2)=[O:19])[CH:13]=1)(C)(C)C>CO>[NH2:29][C:27]1[C:28]2[C:20]([C:18]([C:14]3[CH:15]=[CH:16][CH:17]=[C:12]([C:11]#[C:10][CH2:9][NH2:8])[CH:13]=3)=[O:19])=[CH:21][N:22]([CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)[C:23]=2[N:24]=[CH:25][N:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67219053{3-[3-(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester

Product 1

HCID 67219393(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-[3-(3-amino-prop-1-ynyl)-phenyl]-methanoneYield 113.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl (g) was introduced into a solution of {3-[3-(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-prop-2-ynyl}-carbamic acid tert-butyl ester (421 mg, 0.92 mmol) in MeOH (50 mL). After 5 min the reaction was concentrated to afford the title compound as a brown solid (376 mg, 100%). MS: 360.2 (MH+); HPLC Rf: 4.05 min. (HPLC method 4).

Workup

  1. concentrationAfter 5 min the reaction was concentrated

Sources & evidence

ORD record
ord-df23280510894af4bb28f1bd79dd5b4c
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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