Hydrochloric Acid → HCID 68157066, compound

HRID 243159Notes

Reaction equation

C(OC(=O)[NH:7][C@H:8]([C:10](=[O:26])[NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH:19][C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)[CH3:9])(C)(C)C.[ClH:28]>>[ClH:28].[NH2:7][C@@H:8]([CH3:9])[C:10]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH:19][C:20]1[CH:25]=[N:24][CH:23]=[CH:22][N:21]=1)=[O:26]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 68157069HCID 68157069, compound

Product 1

HCID 68157066HCID 68157066, compoundYield 99%

Conditions

Temperature: 60 °C

Procedure

{(S)-1-[4-Fluoro-2-(pyrazin-2-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester (144 mg, 0.38 mmol) was suspended in hydrochloric acid (4.0 M in 1,4-dioxane, 5.0 ml) and heated at 60° C. for 20 minutes, then concentrated in vacuo to yield the title compound (118 mg, 0.38 mmol, 99%). 1H NMR (MeOD, 400 MHz): δ 8.20 (2H, m), 7.96 (1H, d, J=2.7 Hz), 7.59 (1H, dd, J 10.1, 2.7 Hz), 7.53 (1H, dd, J 9.2, 5.9 Hz), 6.96 (1H, td, J 8.3, 2.9 Hz), 4.10 (3H, m), 1.49 (3H, d, J=7.0 Hz).

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ee50b12f06114d75b526b813bd3c3095
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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