Hydrochloric Acid → HCID 178509860, compound

HRID 1909066Notes

Reaction equation

C(OC([N:8]1[C:12]2=[CH:13][N:14]=[CH:15][C:16]([C:17]3[CH:22]=[C:21]([C:23]([C:25]4[NH:52][C:28]5=[N:29][C:30]([N:33]6[CH2:38][CH2:37][CH:36]([O:39][P:40]([O:47]C(C)(C)C)([O:42]C(C)(C)C)=[O:41])[CH2:35][CH2:34]6)=[CH:31][CH:32]=[C:27]5[N:26]=4)=[O:24])[CH:20]=[CH:19][C:18]=3[C:53]#[N:54])=[C:11]2[CH:10]=[CH:9]1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[C:53]([C:18]1[CH:19]=[CH:20][C:21]([C:23]([C:25]2[NH:52][C:28]3=[N:29][C:30]([N:33]4[CH2:38][CH2:37][CH:36]([O:39][P:40](=[O:41])([OH:42])[OH:47])[CH2:35][CH2:34]4)=[CH:31][CH:32]=[C:27]3[N:26]=2)=[O:24])=[CH:22][C:17]=1[C:16]1[CH:15]=[N:14][CH:13]=[C:12]2[NH:8][CH:9]=[CH:10][C:11]=12)#[N:54]

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 4-(2-Cyano-5-{5-[4-(di-tert-butoxy-phosphoryloxy)-piperidin-1-yl]-3H-imidazo[4,5-b]pyridine-2-carbonyl}-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester (100 mg, 0.132 mmol) (Step 1) in anhydrous CH2Cl2 (5 mL) at 0° C. was added 4M HCl in Dioxane (0.331 mL, 1.32 mmol, 10 eq) and the solution warmed to 23° C. and stirred for 16 hr. The resulting suspension was concentrated under reduced pressure to afford Phosphoric-acid-mono-(1-{2-[4-cyano-3-(1H-pyrrolo[2,3-c]pyridin-4-yl)-benzoyl]-3H-imidazo-[4,5-b]pyridin-5-yl}-piperidin-4-yl)ester as a red-orange solid (75 mg, 0.122 mmol, 92%). HRMS m/z 544.1523 (M+H)+. 1H NMR (400 MHz, MeOD) δ: 9.24 (1H, s), 8.90 (s, 1H), 8.81 (d, J=8 Hz, 1H), 8.58 (s, 1H), 8.34 (d, J=3 Hz, 1H), 8.23 (d, J=8 Hz, 1H), 8.11 (d, J=9 Hz, 1H), 7.29 (d, J=9.5 Hz, 1H), 6.98 (d, J=2.5 Hz, 1H), 4.63 (m, 1H), 3.98 (m, 2H), 3.77 (m, 2H), 2.08 (m, 2H), 1.94 (m, 2H).

Workup

concentrationThe resulting suspension was concentrated under reduced pressure

Sources & evidence

ORD record: ord-30f7d9e6f0554625912e592a5685d2c5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598217B2

Reaction notes

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