Hydrochloric Acid → HCID 178519756, compound

HRID 1909038Notes

Reaction equation

HRID 1909038 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:20]=[C:19]3[NH:21][C:22]([C:24]([C:26]4[CH:31]=[CH:30][N:29]=[C:28]([C:32]5[C:41]6[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=6)[CH:35]=[N:34][CH:33]=5)[CH:27]=4)=[O:25])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CCOCC>[N:11]1([C:15]2[N:20]=[C:19]3[NH:21][C:22]([C:24]([C:26]4[CH:31]=[CH:30][N:29]=[C:28]([C:32]5[C:41]6[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=6)[CH:35]=[N:34][CH:33]=5)[CH:27]=4)=[O:25])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178452069HCID 178452069, compound

Product 1

HCID 178519756HCID 178519756, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The mixture of 4-[2-(2-Isoquinolin-4-yl-pyridine-4-carbonyl)-3H-imidazo[4.5-b]pyridine-5-yl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (15 mg, 0.03 mmole) and 2 molar HCl in ether (1 ml) was stirred at room temperature for 2 hours. Solvent was removed. Residue was washed with ethyl ether a few times to afford (5-[1,4]diazepan-1-yl-3H-imidazo[4,5-b]pyridine-2-yl)-(2-isoquinolin-4-yl-pyridin-4-yl)-methanone (6 mg, 49%) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 2.26 (m, 2H), 3.34 (m, 2H), 3.48 (m, 2H), 3.89 (m, 2H), 4.15 (m, 2H), 7.16 (m, 1H), 7.95 (m, 1H), 8.20 (m, 3H), 8.41-9.16 (m, 5H), 9.93 (d, J=6.53 Hz, 1H). HR-MS m/z 450.2033 [M+1].

Workup

  1. customSolvent was removed
  2. washResidue was washed with ethyl ether a few times

Sources & evidence

ORD record
ord-f02fa5b7143a44c48e1dfc01de69eee8
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

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