1-Pyrrolidineethanamine → HCID 86703912, compound

HRID 1049910Notes

Reaction equation

HRID 1049910 reaction equation
[NH2:1][C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([OH:17])=O)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.S(Cl)(Cl)=O.[N:25]1([CH2:30][CH2:31][NH2:32])[CH2:29][CH2:28][CH2:27][CH2:26]1>C(Cl)Cl>[NH2:1][C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([NH:32][CH2:31][CH2:30][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:17])[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 24386Thionyl ChlorideHCID 867039033-(4-Aminopyrido[3,2-d]pyrimidin-6-yl)benzoic acid

Product 1

HCID 86703912HCID 86703912, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-benzoic acid 14 (100 mg, 0.39 mmol) in DCM (2 mL) was heated with thionyl chloride (0.11 mL, 0.77 mmol) at 80° C. for 1 hour, the mixture was cooled to room temperature and concentrated to dry, 2-pyrrolidin-1-ylethanamine (CAS 7154-73-6) (0.05 mL, 0.58 mmol) was then added, and was stirred overnight. The reaction mixture was purified with prep HPLC to give pure 3-(4-aminopyrido[3,2-d]pyrimidin-6-yl)-N-(2-(pyrrolidin-1-yl)ethyl)benzamide 24. LC/MS (ESI+): m/z 363 (M+H).

Workup

  1. concentrationconcentrated
  2. customto dry
  3. customThe reaction mixture was purified with prep HPLC

Sources & evidence

ORD record
ord-99d0deb5b38240229d943f36d9b794eb
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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