Hydrochloric Acid → HCID 69276870, compound

HRID 2375921Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH:25]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1.[ClH:33]>CO>[ClH:33].[ClH:33].[ClH:33].[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]3[C:12]4[CH:19]=[C:18]([C:20]5[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=5)[NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of tert-butyl 4-[4-(benzothiazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylate (28.3 mg, 0.063 mmol) in MeOH (3 mL) was added 4 N HCl (aq) (3 mL). The mixture was stirred at 60° C. for 8 h. Solvents were removed under reduced pressure to afford the title compound as yellow solid, which was used directly in the next step without purification. 1H-NMR (DMSO-d6, 400 MHz): δ=2.70 (m, 2H), 3.83 (m, 2H), 6.45 (s, 1H), 6.99 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 8.19 (d, J=8.8 Hz, 1H), 8.36 (s, 1H), 8.68 (s, 1H), 9.07 (s, 1H), 9.44 (s, 1H), 10.32 (s, br, 1H), 12.51 (s, 1H). MS (ES+): m/z 349.06 [MH+]. HPLC: tR=1.73 min (ZQ2000, polar—5 min).

Workup

customSolvents were removed under reduced pressure

Sources & evidence

ORD record: ord-4c502a4964c14366b4af3075c65f36f0
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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