Hydrochloric Acid → 2-(3-Aminopropylamino)thiazole-5-carbaldehyde

HRID 1755464Notes

Reaction equation

HRID 1755464 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)=[N:5][CH:4]=1)=[O:2].Cl.C(OCC)C>C(Cl)Cl>[NH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]1[S:7][C:3]([CH:1]=[O:2])=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86700109tert-Butyl 3-(5-formylthiazol-2-ylamino)propylcarbamate

Product 1

HCID 867001102-(3-Aminopropylamino)thiazole-5-carbaldehydeYield 137.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of material from Example 60 (400 mg, 1.402 mmol) in CH2Cl2 (75 mL) is added HCl, 1.0M in diethyl ether (25 mL, 25.00 mmol) and the resulting pale yellow solution is stirred at room temp for 18 h. The solvent is removed in vacuo to give 356 mg (98%) of the title compound as a bis HCl salt by weight. LC/MS (Condition A): ret. T=0.522 min, (M+H)+ 186.11.

Workup

  1. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-31d910dbfc8f4ee29c12f87a122c83d3
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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