Hydrochloric Acid → 1-{2-Amino-6-[(2-{[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]-pyridin-3-yl}ethanone hydrochloride

HRID 2171584Notes

Reaction equation

HRID 2171584 reaction equation
[C:1]([C:4]1[C:5]([NH:31]C(=O)OC(C)(C)C)=[N:6][C:7]([NH:10][CH2:11][CH2:12][NH:13][C:14]2[N:19]3[CH:20]=[CH:21][N:22]=[C:18]3[CH:17]=[C:16]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:15]=2)=[CH:8][CH:9]=1)(=[O:3])[CH3:2].Cl>O1CCOCC1>[ClH:29].[NH2:31][C:5]1[C:4]([C:1](=[O:3])[CH3:2])=[CH:9][CH:8]=[C:7]([NH:10][CH2:11][CH2:12][NH:13][C:14]2[N:19]3[CH:20]=[CH:21][N:22]=[C:18]3[CH:17]=[C:16]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:15]=2)[N:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59312939Tert-butyl {3-acetyl-6-[(2-{[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]pyridin-2-yl}carbamate

Product 1

HCID 687130931-{2-Amino-6-[(2-{[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]-pyridin-3-yl}ethanone hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

32 mg (0.01 mmol) of tert-butyl {3-acetyl-6-[(2-{[7-(2,4-dichlorophenyl)imidazo[1,2-c]pyrimidin-5-yl]amino}ethyl)amino]pyridin-2-yl}carbamate are dissolved in dioxane (2 ml), and 4M hydrogen chloride in dioxane (2 ml) are added. After stilling at RT for 3 h, the solvent is concentrated in a rotary evaporator, and the residue is purified by preparative HPLC. 11 mg (39% of theory) of the product are obtained as a solid.

Workup

  1. concentrationthe solvent is concentrated in a rotary evaporator
  2. customthe residue is purified by preparative HPLC
  3. custom11 mg (39% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-ed097fa460754c97a66e74d23db312f9
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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