Hydrochloric Acid → HCID 86692140, compound

HRID 527917Notes

Reaction equation

HRID 527917 reaction equation
[CH:1]1([N:6]([CH2:19][C:20]#[CH:21])[C@@H:7]2[CH2:11][CH2:10][N:9]([C:12](OC(C)(C)C)=O)[CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.ClC1[C:25]2[CH:32]=[CH:31][NH:30][C:26]=2[N:27]=[CH:28][N:29]=1.CCN(C(C)C)C(C)C>>[CH:1]1([N:6]([CH2:19][C:20]#[CH:21])[C@@H:7]2[CH2:11][CH2:10][N:9]([C:12]3[C:25]4[CH:32]=[CH:31][NH:30][C:26]=4[N:27]=[CH:28][N:29]=3)[CH2:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 86692134HCID 86692134, compound

Product 1

HCID 86692140HCID 86692140, compound

Procedure

(R)-tert-butyl 3-(cyclopentyl(prop-2-ynyl)amino)pyrrolidine-1-carboxylate (80 mg, 0.27 mmol) was stirred with HCl (in MeOH, 6N, 1 mL) at ambient temperature for 2 h, and then concentrated under reduced pressure. The residue was dissolved in EtOH (3 mL) and treated with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (42 mg, 0.27 mmol) in the presence of DIPEA (53 mg, 0.41 mmol) at the refluxing temperature for overnight. The volatiles were removed and the residue was purified by preparative HPLC to give the title compound. MS (m/z): 310 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOH (3 mL)
  3. customThe volatiles were removed
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f48a022847a94e6298a665cbb79f5c0a
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Reaction notes

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