Hydrochloric Acid → 4-(Benzyloxy)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochloride

HRID 2387475Notes

Reaction equation

HRID 2387475 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:31])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:32]>C(OCC)(=O)C.CCOCC>[ClH:32].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:31])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 24857598MCH-1 antagonist 1

Product 1

HCID 684600444-(Benzyloxy)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 4-(benzyloxy)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (20 mg, 0.049 mmol) in ethyl acetate (1 mL) was treated with anhydrous HCl in Et2O (0.05 mL, 1.0 M). After stirring for 10 min, the solid was isolated by filtration, washed with Et2O, and dried under vacuum to give the title compound (24 mg, quantitative) as an off-white powder: mp 200-202° C. dec; 1H NMR (500 MHz, DMSO-d6) δ 10.42 (s, 1H), 8.23 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 7.79 (s, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.48-7.36 (m, 6H), 6.12 (dd, J=7.6, 2.6 Hz, 1H), 5.99 (d, J=2.6 Hz, 1H), 5.16 (s, 2H), 4.85 (br m, 2H), 3.70 (br m, 2H), 3.51 (br m, 2H), 3.01 (br m, 2H), 1.97 (br m, 2H), 1.84 (br m, 2H); ESI MS m/z 415 [M+H]+.

Workup

  1. customthe solid was isolated by filtration
  2. washwashed with Et2O
  3. customdried under vacuum

Sources & evidence

ORD record
ord-ff7bba59b3e84448aadb89e227a7cb6e
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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