Hydrochloric Acid → HCID 69001664, compound

HRID 1984299Notes

Reaction equation

HRID 1984299 reaction equation
C(OC([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][N:11]2[C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=O)(C)(C)C.[ClH:26]>C(O)=O.CO>[ClH:26].[C@H:12]12[CH2:14][C@H:9]([NH:8][CH2:13]1)[CH2:10][N:11]2[C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69003591HCID 69003591, compound

Product 1

HCID 69001664HCID 69001664, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of (S,S)-5-(1H-indole-2-carbonyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (124 mg, 0.36 mmol) in formic acid was added 5.0 N HCl (75 μL, 1.82 mmol). After 1 h at rt, the solution was diluted with MeOH (30 mL) and concentrated to give a purple solid (87 mg, 99%). MS (ESI): mass calcd. for C14H15N3O, 241.12; m/z found, 242.3 [M+H]+. 1H NMR (MeOD): 7.67-7.63 (m, 1H), 7.49-7.44 (m, 1H), 7.28-7.22 (m, 1H), 7.12-7.05 (m, 1H), 7.01-6.97 (m, 1H), 5.49 (s, 1H), 5.41-5.02 (m, 1H), 4.58 (s, 1H), 4.28-3.39 (m, 4H), 3.33-3.29 (m, 1H), 2.32-2.21 (m, 1H), 2.13-2.04 (m, 1H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-67abfa138bea4b5cae86f1e39bcb3abe
Source dataset
uspto-grants-2009_06
Patent number
US07544698B2

Reaction notes

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