Hydrochloric Acid → HCID 58327690, compound

HRID 2039741Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of tert-butyl(3-((5-benzoyl-7H-pyrrolo[2,3-d]pyrimidine-4-yl)amino)benzyl)carbamate (30 mg, 0.068 mmol) in dioxane (0.5 mL) was added 0.5 mL of 4 M HCl in dioxane. The mixture was heated at 50° C. for 1 hour. The solvent was removed under reduced pressure. The residue was washed with DCM and dried on high vacuum to give an off-white solid. M.p.=210-212° C.; 400 MHz 1HNMR (DMSO-d6) δ 13.19 (s, 1H), 11.44 (s, 1H), 8.48 (s, 1H), 8.11 (d, J=8.4 Hz, 2H), 7.98 (s, 1H), 7.87-7.84 (m, 3H), 7.69 (t, J=6.4 Hz, 2H), 7.56 (t, J=7.6 Hz, 2H), 7.46 (t, J=7.6 Hz, 1H), 7.22 (d, J=7.6 Hz, 1H), 5.44 (s, 2H), 4.06 (d, J=6.4 Hz, 2H); LCMS [M+H] 344.

Workup

customThe solvent was removed under reduced pressure
washThe residue was washed with DCM
customdried on high vacuum
customto give an off-white solid

Sources & evidence

ORD record: ord-9c52ed5141f74907ac2b84a430f4a8c6
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580803B2

Reaction notes

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