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Hydrochloric Acid → HCID 136360815, compound

HRID 44226
Notes
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Reaction equation

HRID 44226 reaction equation
[N:1]1[N:2]=[C:3]([C:19]2[CH:40]=[CH:39][C:22]([C:23]([N:25]3[CH2:30][CH2:29][CH:28]([NH:31]C(=O)OC(C)(C)C)[CH2:27][CH2:26]3)=[O:24])=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.[ClH:41]>ClCCl.O1CCOCC1>[ClH:41].[N:1]1[N:2]=[C:3]([C:19]2[CH:40]=[CH:39][C:22]([C:23]([N:25]3[CH2:26][CH2:27][CH:28]([NH2:31])[CH2:29][CH2:30]3)=[O:24])=[CH:21][CH:20]=2)[N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136163790tert-butyl (1-(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoyl)piperidin-4-yl)carbamate

Product 1

HCID 136360815HCID 136360815, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-Dioxane
Solvent

Procedure

To a solution of tert-butyl (1-(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoyl)piperidin-4-yl)carbamate (0.25 g, 0.47 mmol) in dichloromethane (10 mL) was added 4N HCl in dioxane (0.5 mL). The reaction mixture was stirred at room temperature for 20 hours. The solids were filtered off, washed with ether and dried under vacuum, yielding (4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenyl)(4-aminopiperidin-1-yl)methanone hydrochloride as a yellow solid (0.21 g, 88%). M.p.=258-263° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.83 (br.s, 1H), 8.25-8.18 (m, 3H), 7.97 (dd, J=7.6, 1.2 Hz, 1H), 7.51 (d, J=8.0 Hz, 2H), 7.48-7.42 (m, 3H), 7.36 (d, J=8.4 Hz, 1H), 7.20 (dd, J=8.0, 1.2 Hz, 1H), 7.15 (t, J=7.2 Hz, 1H), 6.94 (dd, J=8.0, 4.4 Hz, 1H), 4.55-4.4 (m, 1H), 3.7-3.65 (m, 1H), 3.35-3.25 (m, 1H), 3.22-3.05 (m, 1H), 3.0-2.8 (m, 1H), 2.2-1.85 (m, 2H), 1.6-1.4 (m, 2H); LCMS [M+H]: 438.

Workup

  1. filtrationThe solids were filtered off
  2. washwashed with ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-fc7914a57353476aa33999980b42aee8
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541407B2

Reaction notes

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