Hydrochloric Acid → (S)-N-(3-(5-(2-(2-aminopropylamino)pyrimidin-4-yl)-2-cyclopropyl-1H-imidazol-4-yl)-2-chlorophenyl)propane-1-sulfonamide

HRID 535771Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][C:3]=1[C:15]1[N:16]=[C:17]([CH:46]2[CH2:48][CH2:47]2)[N:18](COCC[Si](C)(C)C)[C:19]=1[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][CH2:27][C@@H:28]([NH:30]C(=O)OC(C)(C)C)[CH3:29])[N:21]=1.Cl>CCO>[NH2:30][C@@H:28]([CH3:29])[CH2:27][NH:26][C:22]1[N:21]=[C:20]([C:19]2[NH:18][C:17]([CH:46]3[CH2:48][CH2:47]3)=[N:16][C:15]=2[C:3]2[C:2]([Cl:1])=[C:7]([NH:8][S:9]([CH2:12][CH2:13][CH3:14])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=2)[CH:25]=[CH:24][N:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of (S)-tert-butyl 1-(4-(4-(2-chloro-3-(propylsulfonamido)phenyl)-2-cyclopropyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate (116 mg, 0.14 mmol) in EtOH (2 mL) was treated with aqueous 6.0 N HCl solution (0.8 mL, 4.8 mmol) and the resulting reaction was heated to 60° C. for 30 minutes, then at room temperature for 40 minutes. The reaction was allowed to cool to room temperature and the volatiles were removed in vacuo. Further drying under high vacuum afforded (S)—N-(3-(5-(2-(2-aminopropylamino)pyrimidin-4-yl)-2-cyclopropyl-1H-imidazol-4-yl)-2-chlorophenyl)propane-1-sulfonamide (80 mg, 0.15 mmol) as the HCl salt (4A-2) which was used without further purification: LCMS (m/z) 490.2 (MH+), tR=0.48 minute.

Workup

customthe resulting reaction
temperatureto cool to room temperature
customthe volatiles were removed in vacuo
customFurther drying under high vacuum

Sources & evidence

ORD record: ord-8a5903f980724b85bcba61c2f58e2f03
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859548B2

Reaction notes

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