Hydrochloric Acid → (1S,3S,4R)-3-amino-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-N,N-dimethylcyclopentanecarboxamide

HRID 56394Notes

Reaction equation

HRID 56394 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([NH:23][C@@H:24]1[CH2:28][C@H:27]([C:29](=[O:33])[N:30]([CH3:32])[CH3:31])[CH2:26][C@@H:25]1[NH:34]C(=O)OC(C)(C)C)[N:17]=[CH:16]2.Cl>C(Cl)Cl.O1CCOCC1>[NH2:34][C@@H:25]1[C@H:24]([NH:23][C:18]2[N:17]=[CH:16][C:15]3[C:20](=[CH:21][CH:22]=[C:13]([C:3]4[C:4]([Cl:12])=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=4[Cl:1])[CH:14]=3)[N:19]=2)[CH2:28][C@@H:27]([C:29]([N:30]([CH3:32])[CH3:31])=[O:33])[CH2:26]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131736923HCID 131736923, compound

Product 1

HCID 118036144(1S,3S,4R)-3-amino-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-N,N-dimethylcyclopentanecarboxamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-butyl ((1S,2R,4S)-2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-4-(dimethylcarbamoyl)cyclopentyl)carbamate (0.062 g, 0.103 mmol) was taken up in DCM (2 ml) and treated with 4M HCl in dioxane (3 ml) and stirred for 3 hours. The solvent was removed to give crude (1S,3S,4R)-3-amino-4-((6-(2,6-dichloro-3,5-dimethoxyphenyl)quinazolin-2-yl)amino)-N,N-dimethylcyclopentane-1-carboxamide, quantative yield. MS (ES+) C24H27Cl2N5O3 requires: 504, found: 505 [M+H]+.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-9870df82442f4a7ebd01f77cbf0f16f5
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

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