Hydrochloric Acid → HCID 9868697, compound

HRID 1057515Notes

Reaction equation

HRID 1057515 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]2[CH:6]([CH2:27][C:28]([O:30]C)=[O:29])[CH2:7][CH2:8][N:9]([C:11](=[O:26])[NH:12][CH2:13][CH2:14][CH2:15][C:16]3[N:21]=[C:20]4[NH:22][CH2:23][CH2:24][CH2:25][C:19]4=[CH:18][CH:17]=3)[CH2:10][C:4]=2[CH:3]=1.O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]2[CH:6]([CH2:27][C:28]([OH:30])=[O:29])[CH2:7][CH2:8][N:9]([C:11](=[O:26])[NH:12][CH2:13][CH2:14][CH2:15][C:16]3[N:21]=[C:20]4[NH:22][CH2:23][CH2:24][CH2:25][C:19]4=[CH:18][CH:17]=3)[CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 69157953methyl 2-{8-chloro-2-[N-(3-(1,2,3,4-tetrahydropyridino[2,3-b]pyridin-7-yl)propyl)carbamoyl]-1H,3H,4H,5H-benzo[e]azepin-5-yl}acetate

Product 1

HCID 9868697HCID 9868697, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of methyl 2-{8-chloro-2-[N-(3-(1,2,3,4-tetrahydropyridino[2,3-b]pyridin-7-yl)propyl)carbamoyl]-1H,3H,4H,5H-benzo[e]azepin-5-yl}acetate (1 eq) in tetrahydrofuran (0.05 M) and water (0.05 M) was added lithium hydroxide monohydrate (1.5 eq). The reaction mixture was stirred at room temperature for 10 h. 1 M of hydrogen chloride (1.5 eq) was added and the reaction solvent was evaporated in vacuo. The residue was diluted with (5% MeOH/CH2Cl2 and the precipitate was filtered. The filtrate was concentrated and dried under vacuum oven for 24 h to afford product. EI-MS m/z 457 (M+H)+; 1H NMR (CD3OD; 400 MHz): δ7.53 (d, J=7.3 Hz, 1H), 7.39 (s, 1H), 7.18 (s, 2H), 6.51 (d, 7.3 Hz, 1H), 4.56 (s, 2H), 3.80-3.45 (m, 5H), 3.21 (m, 2H), 2.80 (m, 4H), 2.75 (m, 2H), 2.00-1.50 (m, 6H).

Workup

  1. customthe reaction solvent was evaporated in vacuo
  2. additionThe residue was diluted with (5% MeOH/CH2Cl2
  3. filtrationthe precipitate was filtered
  4. concentrationThe filtrate was concentrated
  5. customdried under vacuum oven for 24 h
  6. customto afford product

Sources & evidence

ORD record
ord-c2b41d96eca64b42bc72fde2bd2b281f
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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